Allylbenzene

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Reactions (440)

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Substances (2)

Citations (416)

Conditions

References A

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With triethylamine tris(hydrogen fluoride); [Et2NSF2]BF4 in dichloromethane

T=-78 - 20°C; 3 h; Inert atmosphere;

Lheureux, Alexandre; Beaulieu, Francis; Bennett, Christopher; Bill, David R.; Clayton, Simon; Laflamme, Franois; Mirmehrabi, Mahmoud; Tadayon, Sam; Tovell, David; Couturier, Michel

Journal of Organic Chemistry, 2010 , vol. 75, # 10 p. 3401 - 3411 Title/Abstract

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Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 2 h 2: molybdenum trioxide; cesium fluoride; water / acetonitrile / 1.5 h / 100 °C View Scheme

Said, Madhukar S.; Khandare, Lina; Shinde, Sandip S.

Tetrahedron Letters, 2017 , vol. 58, # 1 p. 59 - 62 Title/Abstract

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2

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Multi-step reaction with 3 steps 1: molybdenum trioxide; cesium fluoride; water / acetonitrile / 0.65 h / 100 °C / |Inert atmosphere 2: triethylamine / dichloromethane / 2 h 3: molybdenum trioxide; cesium fluoride; water / acetonitrile / 1.5 h / 100 °C View Scheme

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Said, Madhukar S.; Khandare, Lina; Shinde, Sandip S.

Tetrahedron Letters, 2017 , vol. 58, # 1 p. 59 - 62 Title/Abstract

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B: 64%

With molybdenum trioxide; water; cesium fluoride in acetonitrile

T=100°C; 1.5 h; chemoselective reaction;

Said, Madhukar S.; Khandare, Lina; Shinde, Sandip S.

Tetrahedron Letters, 2017 , vol. 58, # 1 p. 59 - 62 Title/Abstract

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A: 7 %Spectr.

With chloropyridinecobaloxime(III); tetrakis(tetrabutylammonium)decatungstate(VI) in

Abrams, Dylan J.; West, Julian G.; Sorensen, Erik J.

Chemical Science, 2017 , vol. 8, # 3 p. 1954 - 1959

B: 7 %Spectr.

[D3]acetonitrile

T=31°C; 96 h; Inert atmosphereUV-irradiationMolecular sieve; Overall yield = 14 percentSpectr.;

Title/Abstract

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5

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Rx-ID: 3566484 Find similar reactions

71%

With pyridine; lead(IV) acetate; copper diacetate in benzene

8 h; Heating;

Bhat, K. S.; Joshi, P. L.; Rao, A. S.

Synthesis, 1984 , # 2 p. 142 - 145 Title/Abstract

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66%

With 2,2-dimethylpropanoic anhydride; bis[2-(diphenylphosphino)phenyl] ether; palladium dichloride in various solvent(s) T=110°C; 16 h;

Goossen, Lukas J.; Rodriguez, Nuria

Chemical Communications, 2004 , # 6 p. 724 - 725 Title/Abstract

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With acetic anhydride; triethylamine; P(O)Ph2PPh2; palladium dichloride in 1,3 dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone

T=110°C; 18 h; Inert atmosphere;

Notre, Jerome Le; Scott, Elinor L.; Franssen, Maurice C. R.; Sanders, Johan P. M.

Tetrahedron Letters, 2010 , vol. 51, # 29 p. 3712 - 3715 Title/Abstract

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73 %Spectr.

With bis(triphenylphosphine)iridium(I) carbonyl chloride; acetic anhydride; potassium iodide

T=160°C; 5 h; Inert atmosphere;

Maetani, Shinji; Fukuyama, Takahide; Suzuki, Nobuyoshi; Ishihara, Daisuke; Ryu, Ilhyong

Organometallics, 2011 , vol. 30, # 6 p. 1389 - 1394 Title/Abstract

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58 %Spectr.

With carbon monoxide; 1,5-bis-(diphenylphosphino)pentane; acetic anhydride; potassium iodide; iron(II) chloride

T=240°C; P=15201 Torr; 3 h;

Maetani, Shinji; Fukuyama, Takahide; Suzuki, Nobuyoshi; Ishihara, Daisuke; Ryu, Ilhyong

Chemical Communications, 2012 , vol. 48, # 19 p. 2552 - 2554 Title/Abstract

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With P450 peroxygenase OleTJE; NAD; ammonium formate in dimethyl sulfoxide

Wang, Jian-Bo; Lonsdale, Richard; Reetz, Manfred T.

Chemical Communications, 2016 , vol. 52, # 52 p. 8131 - 8133 Title/Abstract

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T=30°C; 24 h; Enzymatic reaction; Catalytic behavior;

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With hydrogen in toluene

T=20°C; P=38002.6 Torr; 12 h; Autoclave; chemoselective reaction;

Rx-ID: 39347803 Find similar reactions

Mitsudome, Takato; Yamamoto, Masaaki; Maeno, Zen; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi

Journal of the American Chemical Society, 2015 , vol. 137, # 42 p. 13452 - 13455

Title/Abstract

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96%

With hydrogen in ethanol

T=20°C; P=760.051 Torr; 3 h;

Mitsudome, Takato; Urayama, Teppei; Yamazaki, Kenji; Maehara, Yosuke; Yamasaki, Jun; Gohara, Kazutoshi; Maeno, Zen; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi

ACS Catalysis, 2016 , vol. 6, # 2 p. 666 - 670 Title/Abstract

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66%

With Au0998Ag0002; hydrogen; diethylamine

T=90°C; P=6080.41 Torr; 24 h; chemoselective reaction;

Takale, Balaram S.; Feng, Xiujuan; Lu, Ye; Bao, Ming; Jin, Tienan; Minato, Taketoshi; Yamamoto, Yoshinori

Journal of the American Chemical Society, 2016 , vol. 138, # 32 p. 10356 - 10364 Title/Abstract

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90 %Spectr.

With formic acid; Au9924Ag0.76; triethylamine in N,N-dimethyl-formamide

T=70°C; 4 h; Inert atmosphereGreen chemistry; chemoselective reaction;

Wagh, Yogesh S.; Asao, Naoki

Journal of Organic Chemistry, 2015 , vol. 80, # 2 p. 847 - 851 Title/Abstract

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With carbon monoxide; hydrogen in tetrahydrofuran

T=70°C; P=7757.43 Torr; 6 h; Autoclave; Hide Experimental Procedure

Jagtap, Samadhan A.; Sasaki, Takehiko; Bhanage, Bhalchandra M.

Journal of Molecular Catalysis A: Chemical, 2016 , vol. 414, p. 78 - 86 Title/Abstract

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2.3. General experimental procedure for synthesis of alkenes viasemi-hydrogenation of alkynes

General procedure: To a 100 mL high-pressure reactor, phenylacetylene (1 mmol),Pd (0.96 molpercent) in a 10 mL THF were transferred under an inertatmosphere. The reactor was flushed three times with nitrogen then pressurized with desired 150 psi of syngas, then heated at70C with constant stirring (400 rpm) for 6 h. After the comple-tion of reaction, the reactor cooled down to room temperature andthe remaining syngas was carefully depressurized. The resultantreaction mixture filtered off by simple filtration. The filtrate was then collected in sample vial and the product was extracted for fur-ther analysis such as GC, GC–MS,1H &13C NMR and matched with those of authentic data. Selective experiments were performed in triplicate and it was observed that results showed variation of ±2percent.

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A: 13% B: 10% C: 77%

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With formic acid; C63H65O3P3Pd3S4; triethylamine in tetrahydrofuran

6 h; Inert atmosphereSchlenk techniqueReflux; Catalytic behavior; Reagent/catalystTime;

Monfredini, Anna; Santacroce, Veronica; Deyris, Pierre-Alexandre; Maggi, Raimondo; Bigi, Franca; Maestri, Giovanni; Malacria, Max

Dalton Transactions, 2016 , vol. 45, # 40 p. 15786 - 15790 Title/Abstract

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With formic acid; C66H72P3Pd3S3(1+)*F6Sb(1-); triethylamine in tetrahydrofuran 10 h; Schlenk techniqueInert atmosphereReflux; Reagent/catalyst; stereoselective reaction;

Deyris, Pierre-Alexandre; Cañeque, Tatiana; Wang, Yanlan; Retailleau, Pascal; Bigi, Franca; Maggi, Raimondo; Maestri, Giovanni; Malacria, Max

ChemCatChem, 2015 , vol. 7, # 20 p. 3266 - 3269 Title/Abstract

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Rx-ID: 42986294 Find similar reactions

42%

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Mastalir, Matthias; Stöger, Berthold; Pittenauer, Ernst; Allmaier, Günter; Kirchner, Karl

Organic Letters, 2016 , vol. 18, # 13 p. 3186 - 3189 Title/Abstract

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With potassium phosphate; C17H36ClN6NiP2(1+)*Cl(1-) in toluene T=135°C; Suzuki-Miyaura Coupling; 16 h; Inert atmosphere;

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With (5-diphenylphosphanyl-9,9-dimethyl-xanthen-4-yl)-diphenylphosphane; lithium chloride; palladium dichloride; 1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene

T=190°C; chemoselective reaction; Hide Experimental Procedure

Rx-ID: 43143969 Find similar reactions

Tolman, William Baker; Hillmyer, Marc A.; John, Alex; Hogan, Levi Thomas

Patent: US2016/194276 A1, 2016 ; Location in patent: Paragraph 0087-0088 ; Title/Abstract

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7.7A:

For each reaction, the fatty acid ester was fed at a concentration of 0.449 mmol. A PdCl2 catalyst was introduced to the reaction mixture at 2.5 mol. percent. Each of the Xantphos and IPr ligands were at 5 mol. percent in the reaction mixture. One equivalent of LiCl with respect to the fatty acid ester was also added to the reaction mixture, e.g., 0.449 mmol. Each reaction mixture was heated to 190° C., and held for 2.5 hours. For each fatty acid ester investigated, the conversion was approximately 90percent. Table 6 shows results of trials for the p-nitrophenol ester of various fatty acids A

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A: 14.9% B: 85.1%

With Carbowax 400; PdCl2(Ph2PCH2CH2CH2SO3K)2; potassium formiate in nheptane; water

T=90°C; other complexes; other polyethers; other allyl and benzyl chlalogenides; Product distribution;

Paetzold, E.; Oehme, G.

Journal fuer Praktische Chemie/Chemiker-Zeitung, 1993 , vol. 335, # 2 p. 181 - 184 Title/Abstract

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With Chromium (III) chloride; lithium aluminium tetrahydride; isopropyl alcohol in tetrahydrofuran; N,N-dimethyl-formamide

T=20°C;

Omoto, Mineko; Kato, Nobuo; Sogon, Tetsuya; Mori, Akira

Tetrahedron Letters, 2001 , vol. 42, # 5 p. 939 - 941 Title/Abstract

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With 1-allyl-2,2,3-trimethyl-1-phenylphosphetanium bromide; lithium tri-tbutoxyaluminum hydride in tetrahydrofuran; N-dodecane; toluene

T=90°C; 16 h; Reagent/catalyst; Overall yield = 98 percent; regioselective reaction;

Reichl, Kyle D.; Dunn, Nicole L.; Fastuca, Nicholas J.; Radosevich, Alexander T.

Journal of the American Chemical Society, 2015 , vol. 137, # 16 p. 5292 - 5295 Title/Abstract

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11

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Rx-ID: 1620008 Find similar reactions

With C11H22P(1+)*Br(1-); lithium tri-t-butoxyaluminum hydride in tetrahydrofuran; N-dodecane; toluene

T=90°C; 16 h; Reagent/catalyst; regioselective reaction;

Reichl, Kyle D.; Dunn, Nicole L.; Fastuca, Nicholas J.; Radosevich, Alexander T.

Journal of the American Chemical Society, 2015 , vol. 137, # 16 p. 5292 - 5295 Title/Abstract

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With hydrogenchloride; indium

1.) DMF, 1 h, RT, 2.) 1 min; Yield given. Multistep reaction;

Araki, Shuki; Shimizu, Toshio; Johar, Perminder S.; Jin, Shun-Ji; Butsugan, Yasuo

Journal of Organic Chemistry, 1991 , vol. 56, # 7 p. 2538 - 2542 Title/Abstract

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A: 30 % Chromat.

B: 60 % Chromat.

With zinc-modified cyanoborohydride in diethyl ether

0.5 h; Ambient temperature;

Kim, Sunggak; Kim, Yong Jin; Ahn, Kyo Han

Tetrahedron Letters, 1983 , vol. 24, # 32 p. 3369 - 3372 Title/Abstract

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A: 30 % Chromat.

B: 60 % Chromat.

With zinc-modified cyanoborohydride in diethyl ether

0.5 h; Ambient temperature;

Kim, Sunggak; Kim, Yong Jin; Ahn, Kyo Han

Tetrahedron Letters, 1983 , vol. 24, # 32 p. 3369 - 3372 Title/Abstract

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With 1-allyl-2,2,3-trimethyl-1-phenylphosphetanium bromide; lithium tri-tbutoxyaluminum hydride in tetrahydrofuran; N-dodecane; toluene

T=90°C; 16 h; Reagent/catalyst; Overall yield = 96 percent; regioselective reaction;

Reichl, Kyle D.; Dunn, Nicole L.; Fastuca, Nicholas J.; Radosevich, Alexander T.

Journal of the American Chemical Society, 2015 , vol. 137, # 16 p. 5292 - 5295 Title/Abstract

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With lithium tri-t-butoxyaluminum hydride in tetrahydrofuran; Ndodecane; toluene

T=90°C; 16 h; Reagent/catalyst; Overall yield = 80 percent; regioselective reaction;

Reichl, Kyle D.; Dunn, Nicole L.; Fastuca, Nicholas J.; Radosevich, Alexander T.

Journal of the American Chemical Society, 2015 , vol. 137, # 16 p. 5292 - 5295 Title/Abstract

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13

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70%

Rx-ID: 6330287 Find similar reactions

Stage #1: With magnesium; lithium chloride in tetrahydrofuran

T=20°C; Inert atmosphere; Stage #2: With iron (III) acetylacetonate in tetrahydrofuran

T=0°C; 0.0833333 h; Stage #3: in tetrahydrofuran

2 h; Hide Experimental Procedure

SALTIGO GMBH; Gotta, Matthias; Lehnemann, Bernd Wilhelm; Czaplik, Waldemar Maximilian; Mayer, Matthias; Jacobi Von Wangelin, Axel

Patent: US2013/184485 A1, 2013 ; Location in patent: Paragraph 0062; 0063; 0064 ; Title/Abstract

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3:Coupling of Allyl Acetate with 2-methoxyphenylmagnesium Bromide

General procedure: Example 1 Coupling of Allyl Acetate with 2-methoxyphenylmagnesium Bromide Under protective gas, 63 mg of magnesium turnings, 126 mg of anhydrous lithium chloride, 4 ml of dry tetrahydrofuran and 2.4 mmol of 2-bromoanisole were reacted at room temperature to give the Grignard compound.Then the dark-colored solution formed was cooled to 0° C. and a solution of 35.3 mg of iron(III) acetylacetonate (5 mol percent) in 2 ml of dry tetrahydrofuran was added and the mixture was stirred for five minutes. Then 2 mmol of allyl acetate were added dropwise and the reaction mixture was stirred for 2 h. For workup, hydrolysis was effected with 5 ml of saturated sodium hydrogencarbonate solution and the mixture was extracted three times with 10 ml each time of ethyl acetate. The combined organic phases were dried over magnesium sulfate, concentrated and purified by column chromatography on silica gel (eluent: cyclohexane-ethyl acetate). 95percent of theory of 2-allylanisole was isolated.

Cramer,F.; Hennrich,N.

Chemische Berichte, 1961 , vol. 94, p. 976 - 989 Full Text View citing articles Show Details

Huettel,R.; Kochs,P.

Chemische Berichte, 1968 , vol. 101, p. 1043 - 1048 Full Text View citing articles Show Details

Sucrow,W.

Chemische Berichte, 1968 , vol. 101, p. 4230 - 4237 Full Text View citing articles Show Details

Heck,R.F.

Journal of the American Chemical Society, 1968 , vol. 90, p. 5538 - 5542 Full Text View citing articles Show Details

LaRochelle,R.W.; Trost,B.M.

Journal of the American Chemical Society, 1971 , vol. 93, p. 6077 - 6086 Full Text View citing articles Show Details

Heck,R.F.

Journal of the American Chemical Society, 1971 , vol. 93, p. 6896 - 6901 Full Text View citing articles Show Details

Chevalier,P. et al.

Bulletin de la Societe Chimique de France, 1975 , p. 2254 - 2258 Full Text View citing articles Show Details

Nakai,T. et al.

Chemistry Letters, 1975 , p. 249 - 252 Full Text View citing articles Show Details

Berlin,K.D. et al.

Journal of Organic Chemistry, 1969 , vol. 34, p. 1266 - 1271 Full Text View citing articles Show Details

Sato,K. et al.

Journal of Organic Chemistry, 1972 , vol. 37, # 3 p. 462 - 466 Full Text View citing articles Show Details

Hutchins,R.O. et al.

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Tetrahedron Letters, 1976 , p. 3487 - 3490 Full Text View citing articles Show Details

Baker,R.; Spillett,M.J.

Journal of the Chemical Society [Section] B: Physical Organic, 1969 , p. 581 - 588 Full Text View citing articles Show Details

Ando,W.; Sekiguchi,A.

Journal of Organometallic Chemistry, 1977 , vol. 133, p. 219 - 230 Full Text View citing articles Show Details

Bumgardner; Freeman

Journal of the American Chemical Society, 1964 , vol. 86, p. 2233

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Hutchins et al.

Journal of the American Chemical Society, 1973 , vol. 95, p. 3662,3665 Full Text Show Details

Opitz; Fischer

Angewandte Chemie, 1965 , vol. 77, p. 41 Full Text Show Details

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Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1965 , vol. 261, p. 1699 Full Text Show Details

Mihailovic et al.

Helvetica Chimica Acta, 1973 , vol. 56, p. 3056 Full Text Show Details

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Journal of Organic Chemistry, 1970 , vol. 35, p. 303 Full Text View citing articles Show Details

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Journal of Organic Chemistry, 1964 , vol. 29, p. 121,122 Full Text Show Details

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Journal of Organic Chemistry, 1970 , vol. 35, p. 347 Full Text View citing articles Show Details

Malinowskii; Prib

J. Gen. Chem. USSR (Engl. Transl.), 1963 , vol. 33, p. 1086,1073 Full Text Show Details

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Journal of the Chemical Society [Section] C: Organic, 1966 , p. 578 Full Text Show Details

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Bayer A.-G.

Patent: NL6504228 , 1964 ; Chem.Abstr., 1966 , vol. 64, # 17477c Full Text Show Details

Mulzer; Bruentrup

Angewandte Chemie, 1977 , vol. 89, p. 265 Full Text Show Details

Seghers; Shechter

Tetrahedron Letters, 1976 , p. 1943,1944, 1945 Full Text View citing articles Show Details

Miller et al.

Journal of Organometallic Chemistry, 1974 , vol. 82, p. 127,134, 135 Full Text View citing articles Show Details

Butsugan et al.

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Journal of Chemistry of the United Arab Republic, 1966 , vol. 9, p. 145 Full Text Show Details

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Collection of Czechoslovak Chemical Communications, 1974 , vol. 39, p. 3124,3125-3130 Full Text Show Details

Shapiro et al.

Tetrahedron Letters, 1975 , p. 1811,1813 Full Text Show Details

Mueller; Thi Minh Phuong

Tetrahedron Letters, 1978 , p. 4727 Full Text Show Details

Milstein; Stille

Journal of the American Chemical Society, 1979 , vol. 101, p. 4992,4995 Full Text Show Details

Sonnenberg

Journal of Organic Chemistry, 1970 , vol. 35, p. 3166 Full Text View citing articles Show Details

Batsugan et al.

Chemistry Letters, 1973 , p. 703 Full Text Show Details

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Soobshcheniya Akademii Nauk Gruzinskoi SSR, 1977 , vol. 87, p. 627 Chem.Abstr., vol. 88, # 37873e Full Text Show Details

Stefani; Consiglio

Helvetica Chimica Acta, 1972 , vol. 55, p. 117,118 Full Text Show Details

Johnson; Dutra

Journal of the American Chemical Society, 1973 , vol. 95, p. 7777,7781 Full Text Show Details

Jones; Costanzo

Journal of Organic Chemistry, 1973 , vol. 38, p. 3189,3192

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Elphimoff-Felkin; Sarda

Tetrahedron Letters, 1972 , p. 725 Full Text View citing articles Show Details

Kabalka et al.

Journal of Organic Chemistry, 1976 , vol. 41, p. 574 Full Text View citing articles Show Details

Hutchins; Natale

Journal of Organic Chemistry, 1978 , vol. 43, p. 2299 Full Text View citing articles Show Details

Aso et al.

Kogyo Kagaku Zasshi, 1967 , vol. 70, p. 1001,1002, 1005 Full Text Show Details

Domrachev et al.

J. Gen. Chem. USSR (Engl. Transl.), 1971 , vol. 41, p. 1924,1938 Full Text Show Details

Sato; Inoue

Kenkyu Hokoku - Asahi Garasu Kogyo Gijutsu Shoreikai, 1971 , vol. 19, p. 259,262 Chem.Abstr., vol. 77, # 140318z Full Text Show Details

Union Carbide Corp.

Patent: US3185743 , 1958 ; Chem.Abstr., 1965 , vol. 63, # 2896h Full Text Show Details

Low; Lee

Journal of the Chemical Society [Section] B: Physical Organic, 1970 , p. 535,536, 537, 538 Full Text View citing articles Show Details

Chuit et al.

Chemical Communications (London), 1968 , p. 1604 Full Text View citing articles Show Details

Okamura; Takei

Tetrahedron Letters, 1979 , p. 3425,3427 Full Text Show Details

Frey; Midcalfe

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Australian Journal of Chemistry, 1973 , vol. 26, p. 1529 Full Text Show Details

Migita et al.

Tetrahedron, 1973 , vol. 29, p. 51,53 Full Text Show Details

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Journal of Organometallic Chemistry, 1977 , vol. 127, p. 371,373, 381 Full Text View citing articles Show Details

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Chemical Communications (London), 1966 , p. 757 Full Text View citing articles Show Details

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Isotopenpraxis, 1978 , vol. 14, p. 389 Full Text Show Details

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Journal of Organic Chemistry, 1972 , vol. 37, p. 1676 Full Text View citing articles Show Details

Gamboa et al.

Anales de la Real Sociedad Espanola de Fisica y Quimica, Serie B: Quimica, 1961 , vol. 57, p. 607,612 Full Text Show Details

Martin; Gleicher

Journal of the American Chemical Society, 1964 , vol. 86, p. 233,234 Full Text Show Details

Martin; Jensen

Journal of Organic Chemistry, 1962 , vol. 27, p. 1201,1202 Full Text Show Details

Schnikin; Posdnjak

Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1965 , p. 329 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1965 , p. 353 Full Text Show Details

Gelli et al.

Annali di Chimica (Rome, Italy), 1964 , vol. 54, p. 1143,1146 Full Text Show Details

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Synthetic Communications, 1979 , vol. 9, p. 275 Full Text Show Details

Schichmamedbekowa et al.

Azerbaidzhanskii Khimicheskii Zhurnal, 1975 , vol. 1, p. 27,31 Chem.Abstr., 1975 , vol. 83, # 78768 Full Text Show Details

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Journal of the American Chemical Society, 1968 , vol. 90, p. 5211 Full Text View citing articles Show Details

Laurent et al.

Bulletin de la Societe Chimique de France, 1967 , p. 1995 Full Text Show Details

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Bodrikov; Okrokova

Journal of Organic Chemistry USSR (English Translation), 1967 , vol. 3, p. 1663 Zhurnal Organicheskoi Khimii, 1967 , vol. 3, p. 1706 Full Text Show Details

Brown; Sharp

Journal of the American Chemical Society, 1968 , vol. 90, p. 2915 Full Text View citing articles Show Details

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Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1968 , vol. 266, p. 1611 Full Text Show Details

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YAMANOUCHI PHARMACEUTICAL CO., LTD.

Patent: EP820989 A1, 1998 ; Title/Abstract

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In consequence, illustrative examples of the lower alkylene group which may be substituted with hydroxyl group, an aryl group or an oxo group include hydroxymethylene ... benzylmethylene phenylethylene benzylethylene phenyltrimethylene ...

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MERRELL DOW PHARMACEUTICALS INC.

Patent: EP410380 A2, 1991 ; Title/Abstract

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Illustrative examples of terminal olefins, i.e., compounds of formula II, which can be fluorinated by this method include: ...

3-phenyl-1-butene 3-(2-thienyl)-1-butene allylbenzene 1,9-decadiene ...

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Jensen, Vidar R.; Occhipinti, Giovanni

Patent: US2015/25212 A1, 2015 ; Location in patent: Page/Page column ; Title/Abstract

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9:Homocoupling of Allylbenzene Using 4a in Presence of Air (in Solution)

Example 9 Homocoupling of Allylbenzene Using 4a in Presence of Air (in Solution) In the fume hood, a 50 mL Schlenk flask equipped with a Young's tap and a magnetic stirring bar was charged with the catalyst (0.005 mmol), and with 2 mmol of substrate (stored under air).

The solvent (stored under air) was added to the flask to obtain 0.5 mL of a 4 M solution.

The Schlenk flask was closed and the reaction mixture was stirred and heated in an oil bath at 40° C.

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Rx-ID: 29884196 Find similar reactions

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70 %Chromat.

Stage #1: bromobenzene With magnesium; lithium chloride in tetrahydrofuran

T=20°C; 2 h; Inert atmosphere; Stage #2: With iron (III) acetylacetonate in tetrahydrofuran

T=0°C; 0.0833333 h; Inert atmosphere; Stage #3: ethylene,methyl acetate in tetrahydrofuran

T=0°C; 0.75 h; Inert atmosphere;

Mayer, Matthias; Czaplik, Waldemar M.; Von Wangelin, Axel Jacobi

Advanced Synthesis and Catalysis, 2010 , vol. 352, # 13 p. 2147 - 2152 Title/Abstract

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Stage #1: bromobenzene With magnesium; lithium chloride in tetrahydrofuran

T=20°C; 2 h; Inert atmosphere; Stage #2: With iron (III) acetylacetonate in tetrahydrofuran

0.0833333 h; Inert atmosphere; Stage #3: ethylene,methyl acetate in tetrahydrofuran

T=0°C; 0.75 h; Inert atmosphere;

Bagal, Dattatraya B.; Kachkovskyi, Georgiy; Knorn, Matthias; Rawner, Thomas; Bhanage, Bhalchandra M.; Reiser, Oliver

Angewandte Chemie - International Edition, 2015 , vol. 54, # 24 p. 6999 - 7002 Angew. Chem., 2015 , vol. 127, # 24 Title/Abstract

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A

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With formic acid; para-xylene; [Pd(C3H4N2(2,6-diisopropylphenyl)2)(η2-maleic anhydride)2]; triethylamine in acetonitrile

T=80°C; 24 h; Inert atmosphereSchlenk techniqueReflux; Catalytic behavior; chemoselective reaction;

Hauwert, Peter; Dunsford, Jay J.; Tromp, Dorette S.; Weigand, Jan J.; Lutz, Martin; Cavell, Kingsley J.; Elsevier, Cornelis J.

Organometallics, 2013 , vol. 32, # 1 p. 131 - 140 Title/Abstract

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With formic acid; PdII(1,3-bis(mesityl)imidazol-2-ylidene)(allyl) (Cl); triethylamine; triphenylphosphine in acetonitrile

T=70°C; 0.166667 h; Schlenk techniqueInert atmosphere; Reagent/catalyst;

Drost, Ruben M.; Rosar, Vera; Marta, Silvia Dalla; Lutz, Martin; Demitri, Nicola; Milani, Barbara; De Bruin, Bas; Elsevier, Cornelis J.

ChemCatChem, 2015 , vol. 7, # 14 p. 2095 - 2107 Title/Abstract

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A

B

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Rx-ID: 34828188 Find similar reactions

B: > 98 %Chromat.

With trimethylsilyl trifluoromethanesulfonate; triethylamine

A: > 98 %Chromat.

With trimethylsilyl trifluoromethanesulfonate; triethylamine

Inert atmosphere; Hide Experimental Procedure

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Standley, Eric A.; Jamison, Timothy F.

Journal of the American Chemical Society, 2013 , vol. 135, # 4 p. 1585 - 1592 Title/Abstract

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MASSACHUSETTS INSTITUTE OF TECHNOLOGY; JAMISON, Timothy F.; STANDLEY, Eric Alan

Patent: WO2015/70026 A1, 2015 ; Location in patent: Page/Page column 23-24 ; Title/Abstract

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1:

Complex 3 was not isolated; its yield was determined indirectly to be >98 based on the amount of allylbenzene formed (measured by GC). Treatment of complex 2 with benzyl chloride, Et3N, and TESOTf facilitated the benzylation of ethylene to yield allylbenzene and (PCy2Ph)2Ni(0) (3), which is believed to be the catalytically active species. Even at half the catalyst loading (5 mol percent instead of 10 mol percent employed previously), the coupling of benzyl chloride with 1-octene proceeds faster than when Ni(COD)2 and PCy2Ph are used as the catalyst. Furthermore, addition of COD to a reaction catalyzed by 2 retards the rate relative to a control experiment in which no COD was added. Thus, the presence of COD decreased the rate of this coupling reaction.

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Rx-ID: 36343796 Find similar reactions

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40%

With (2-phenylethyl)diphenylphosphane; iron(II) chloride in toluene

T=45°C; Negishi Coupling; 14 h; Inert atmosphere;

Brown, Caleb A.; Nile, Terence A.; Mahon, Mary F.; Webster, Ruth L.

Dalton Transactions, 2015 , vol. 44, # 27 p. 12189 - 12195 Title/Abstract

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98 %Chromat.

in tetrahydrofuran

T=25°C; 0.5 h; Inert atmosphere;

Erdik, Ender; Eroglu, Fatma; Kalkan, Melike; Pekel, Oezgen Oemuer; Oezkan, Duygu; Serdar, Ebru Z.

Journal of Organometallic Chemistry, 2013 , vol. 745-746, p. 235 - 241 Title/Abstract

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in benzene-d6

T=20°C; 0.166667 h; Inert atmosphereGlovebox;

Dunsford, Jay J.; Clark, Ewan R.; Ingleson, Michael J.

Angewandte Chemie, International Edition, 2015 , vol. 54, # 19 p. 5688 - 5692 Angewandte Chemie, 2015 , vol. 127, # 19 p. 5780 - 5784,5 Title/Abstract

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Rx-ID: 36343815 Find similar reactions

Multi-step reaction with 2 steps 1: tetrahydrofuran / 0.25 h / 0 °C / |Inert atmosphere 2: tetrahydrofuran / 0.5 h / 25 °C / |Inert atmosphere View Scheme

Erdik, Ender; Eroglu, Fatma; Kalkan, Melike; Pekel, Oezgen Oemuer; Oezkan, Duygu; Serdar, Ebru Z.

Journal of Organometallic Chemistry, 2013 , vol. 745-746, p. 235 - 241 Title/Abstract

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Multi-step reaction with 2 steps 1: tetrahydrofuran / 0.25 h / 0 °C / |Inert atmosphere 2: tetrahydrofuran / 0.5 h / 25 °C / |Inert atmosphere View Scheme

Erdik, Ender; Eroglu, Fatma; Kalkan, Melike; Pekel, Oezgen Oemuer; Oezkan, Duygu; Serdar, Ebru Z.

Journal of Organometallic Chemistry, 2013 , vol. 745-746, p. 235 - 241 Title/Abstract

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Multi-step reaction with 2 steps 1: tetrahydrofuran / 0.25 h / 0 °C / |Inert atmosphere 2: tetrahydrofuran / 0.5 h / 25 °C / |Inert atmosphere View Scheme

Erdik, Ender; Eroglu, Fatma; Kalkan, Melike; Pekel, Oezgen Oemuer; Oezkan, Duygu; Serdar, Ebru Z.

Journal of Organometallic Chemistry, 2013 , vol. 745-746, p. 235 - 241 Title/Abstract

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Multi-step reaction with 2 steps 1: diethyl ether; tetrahydrofuran / 0.5 h / |Inert atmosphere 2: iron(II) chloride; (2-phenylethyl)diphenylphosphane / toluene / 14 h / 45 °C / |Inert atmosphere View Scheme

Brown, Caleb A.; Nile, Terence A.; Mahon, Mary F.; Webster, Ruth L.

Dalton Transactions, 2015 , vol. 44, # 27 p. 12189 - 12195 Title/Abstract

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A

B

C

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Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0.17 h / |Inert atmosphere 1.2: 20 °C / |Inert atmosphere 2.1: palladium dichloride; lithium chloride / 5 h / 155 - 160 °C / |Inert atmosphere; |Schlenk technique; |Sealed tube View Scheme

A

John, Alex; Hogan, Levi T.; Hillmyer, Marc A.; Tolman, William B.

Chemical Communications, 2015 , vol. 51, # 13 p. 2731 - 2733 Title/Abstract

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C

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Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0.17 h / |Inert atmosphere 1.2: 20 °C / |Inert atmosphere 2.1: palladium dichloride; lithium chloride / 5 h / 155 - 160 °C / |Inert atmosphere; |Schlenk technique; |Sealed tube View Scheme

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John, Alex; Hogan, Levi T.; Hillmyer, Marc A.; Tolman, William B.

Chemical Communications, 2015 , vol. 51, # 13 p. 2731 - 2733 Title/Abstract

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A

B

C

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21

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A: 10 %Spectr.

With lithium chloride; palladium dichloride

T=155 - 160°C; 5 h; Inert atmosphereSchlenk techniqueSealed tube;

John, Alex; Hogan, Levi T.; Hillmyer, Marc A.; Tolman, William B.

Chemical Communications, 2015 , vol. 51, # 13 p. 2731 - 2733 Title/Abstract

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A

B

C

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A: 10 %Spectr.

With lithium chloride; palladium dichloride

T=155 - 160°C; 5 h; Inert atmosphereSchlenk techniqueSealed tube;

John, Alex; Hogan, Levi T.; Hillmyer, Marc A.; Tolman, William B.

Chemical Communications, 2015 , vol. 51, # 13 p. 2731 - 2733

Title/Abstract

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A

B

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23

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With 1-allyl-2,2,3-trimethyl-1-phenylphosphetanium tetraphenylborate; lithium tri-t-butoxyaluminum hydride in tetrahydrofuran; N-dodecane; toluene

T=90°C; 16 h; Reagent/catalyst; Overall yield = 90 percent; regioselective reaction;

Reichl, Kyle D.; Dunn, Nicole L.; Fastuca, Nicholas J.; Radosevich, Alexander T.

Journal of the American Chemical Society, 2015 , vol. 137, # 16 p. 5292 - 5295 Title/Abstract

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A

B

C

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Rx-ID: 40026964 Find similar reactions

C: 22 %Chromat.

With trans-di(μ-acetato)bis[o-(di-otolylphosphino)benzyl]dipalladium(II); potassium carbonate; tris-(otolyl)phosphine in methanol; N,N-dimethyl acetamide

T=90°C; 24 h; Schlenk technique; Hide Experimental Procedure

ETH ZURICH; SARRIA TORO, Juan Manuel; CHEN, Peter; DEN HARTOG, Tim

Patent: WO2015/67696 A1, 2015 ; Location in patent: Page/Page column 4; 5; 7 ; Title/Abstract

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General procedure: In the glove box, a 5 ml . Young Schlenk (approximately 10 mL total volume) was equipped with a glass coated st ir bar. In the glove box, base (1.5 equiv ), methylenat ion reagent ( 1 .5 equiv), olefin (1 equiv). and catalyst (5 molpercent) were transferred to the vial. A degassed solvent mixture of a polar solvent (16 mL/mmol. substrate) and a ROH solvent (2 mL/mmol substrate) were added and the Schlenk was closed. After transferring the Schlenk outside the glove box, the reaction mixture was heated to 90 °C in an oil bath and st irred for 16 h. Then the reaction mixture was ra idly cooled to 0 °C in an ice bath. Consecutively undecane (0.4 equiv) as internal standard, EbO (45 ml . mmol substrate) and water (45 ml. /mmol substrate) were then added. The phases were separated and the aqueous phase was extracted with EbO (45 mL/mmol substrate). The combined organic phases were washed w ith brine (45 mL/mmol substrate), dried over MgS04 and analyzed by GC-MS. A

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A: 85% B: 5%

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With hydrogen in water

T=270°C; P=16501.7 Torr; 3 h;

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Huang, Yao-Bing; Yan, Long; Chen, Meng-Yuan; Guo, Qing-Xiang; Fu, Yao

Green Chemistry, 2015 , vol. 17, # 5 p. 3010 - 3017 Title/Abstract

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A

B

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A: 68% B: 7%

With hydrogen in water

T=270°C; P=16501.7 Torr; 4 h;

Huang, Yao-Bing; Yan, Long; Chen, Meng-Yuan; Guo, Qing-Xiang; Fu, Yao

Green Chemistry, 2015 , vol. 17, # 5 p. 3010 - 3017 Title/Abstract

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90 %Spectr.

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With [Rh(1,5-cyclooctadienyl)(μ-OCH3)]2; 3-methoxy-benzoic acid; 9,9-dimethyl4,5-bis(diphenyl-phosphino)xanthene in tetrahydrofuran

T=40 - 80°C; chemoselective reaction;

Rx-ID: 40077842 Find similar reactions

Murphy, Stephen K.; Park, Jung-Woo; Cruz, Faben A.; Dong, Vy M.

Science, 2015 , vol. 347, # 6217 p. 56 - 60 Title/Abstract

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A

28

B

C

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Rx-ID: 41009824 Find similar reactions

With potassium tert-butylate in tetrahydrofuran-d8

T=25°C; 3 h; Inert atmosphereSchlenk technique; Kinetics;

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Melvin, Patrick R.; Balcells, David; Hazari, Nilay; Nova, Ainara

ACS Catalysis, 2015 , vol. 5, # 9 p. 5596 - 5606 Title/Abstract

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A

B

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29

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Rx-ID: 41009831 Find similar reactions

With potassium tert-butylate in d(4)-methanol

T=25°C; 3 h; Inert atmosphereSchlenk technique; Kinetics; Reagent/catalyst;

Melvin, Patrick R.; Balcells, David; Hazari, Nilay; Nova, Ainara

ACS Catalysis, 2015 , vol. 5, # 9 p. 5596 - 5606 Title/Abstract

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30

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With tetrakis(triphenylphosphine) palladium(0) in dichloromethane

T=20°C; 4 h; Inert atmosphere;

Rx-ID: 41137212 Find similar reactions

Das, Arindam; Wang, Dong; Belhomme, Marie-Charlotte; Szabó, Kálmán J.

Organic Letters, 2015 , vol. 17, # 19 p. 4754 - 4757 Title/Abstract

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31

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Rx-ID: 1564465 Find similar reactions

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69%

With carbon monoxide in water

T=27°C; P=760.051 Torr; 24 h; chemoselective reaction;

Mitsudome, Takato; Noujima, Akifumi; Mikami, Yusuke; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi

Chemistry - A European Journal, 2010 , vol. 16, # 39 p. 11818 - 11821 Title/Abstract

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69%

With carbon monoxide; water

T=27°C; P=760.051 Torr; 24 h; chemoselective reaction;

Noujima, Akifumi; Mitsudome, Takato; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi

Molecules, 2011 , vol. 16, # 10 p. 8209 - 8227 Title/Abstract

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With chromium

Togashi, Shigeo; Fulcher, John G.; Cho, Bong Rae; Hasegawa, Minoru; Gladysz, J.A.

Journal of Organic Chemistry, 1980 , vol. 45, # 15 p. 3044 - 3053 Title/Abstract

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89 %Chromat.

With isopropyl alcohol in toluene

T=110°C; 24 h; Inert atmosphere;

Mitsudome, Takato; Noujima, Akifumi; Mikami, Yusuke; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi

Angewandte Chemie - International Edition, 2010 , vol. 49, # 32 p. 5545 - 5548 Title/Abstract

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96 %Chromat.

With hydrogen in toluene

T=110°C; P=4560.31 Torr; 24 h; Autoclave; chemoselective reaction;

Mitsudome, Takato; Mikami, Yusuke; Matoba, Motoshi; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi

Angewandte Chemie - International Edition, 2012 , vol. 51, # 1 p. 136 - 139 Title/Abstract

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With potassium hydroxide in isopropyl alcohol

T=25°C; Inert atmosphereIrradiation;

Ke, Xuebin; Sarina, Sarina; Zhao, Jian; Zhang, Xingguang; Chang, Jin; Zhu, Huaiyong

Chemical Communications, 2012 , vol. 48, # 29 p. 3509 - 3511 Title/Abstract

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99 %Chromat.

With silver-deposited TiO2 in isopropyl alcohol

T=24.84°C; 1.5 h; Inert atmosphereIrradiation; SolventTime;

Kominami, Hiroshi; Yamamoto, Satoshi; Imamura, Kazuya; Tanaka, Atsuhiro; Hashimoto, Keiji

Chemical Communications, 2014 , vol. 50, # 35 p. 4558 - 4560 Title/Abstract

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A

B

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Rx-ID: 2013160 Find similar reactions

A: 39 % Chromat.

B: 60 % Chromat.

With tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran

T=20°C; 1.5 h; also with other PhM (M = ZnCl, CdBr, AlCl2); Product distribution;

Bumagin, N. A.; Kasatkin, A. N.; Beletskaya, I. P.

Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1984 , vol. 33, p. 1696 - 1703 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1984 , # 8 p. 1858 - 1865 Title/Abstract

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A: 39 % Chromat.

B: 60 % Chromat.

With tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran; diethyl ether

T=20°C; 1.5 h; Product distribution;

Bumagin, N. A.; Kasatkin, A. N.; Beletskaya, I. P.

Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1984 , vol. 33, p. 1696 - 1703 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1984 , # 8 p. 1858 - 1865 Title/Abstract

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A: 9 %Chromat.

B: 17 %Chromat.

Stage #1: phenyl-magnesium bromide With ZnCl2-N,N,N′,N′tetramethylethylenediamine; 1-phenyl-1H-pyrazole in tetrahydrofuran

T=0°C; 0.05 h; Schlenk techniqueInert atmosphere; Stage #2: 3-phenoxy-1-propene With 2,9-dimethyl-1,10-phenanthroline; iron (III) acetylacetonate in tetrahydrofuran

Asako, Sobi; Norinder, Jakob; Ilies, Laurean; Yoshikai, Naohiko; Nakamura, Eiichi

Advanced Synthesis and Catalysis, 2014 , vol. 356, # 7 p. 1481 - 1485 Title/Abstract

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T=0°C; 16 h; Schlenk techniqueInert atmosphere; Catalytic behavior; Reagent/catalyst;

33

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Rx-ID: 9207661 Find similar reactions

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95%

With 2C2H3O2(1-)*Pd(2+)*3Na(1+)*C18H12O9PS3(3-); potassium tertbutylate; glycerol

T=100°C; Suzuki-Miyaura Coupling; 12 h; Schlenk techniqueInert atmosphere;

Chahdoura, Faouzi; Pradel, Christian; Gomez, Montserrat

Advanced Synthesis and Catalysis, 2013 , vol. 355, # 18 p. 3648 - 3660 Title/Abstract

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72%

With potassium tert-butylate; (1,3-di(2,4,6-(CH3)3-C6H2)-imidazol-2ylidene)Pd(OAc)2 in isopropyl alcohol

T=20°C; Suzuki-Miyaura coupling; 0.5 h;

Singh, Rohit; Viciu, Mihai S.; Kramareva, Natalia; Navarro, Oscar; Nolan, Steven P.

Organic Letters, 2005 , vol. 7, # 9 p. 1829 - 1832 Title/Abstract

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71%

With potassium tert-butylate in isopropyl alcohol

T=50°C; 12 h; Inert atmosphere;

Yang, Hengquan; Li, Guang; Ma, Zhancheng; Chao, Jianbin; Guo, Zhiqiang

Journal of Catalysis, 2010 , vol. 276, # 1 p. 123 - 133 Title/Abstract

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69%

With potassium hydroxide; phenone oxime-derived palladacycle; tetrabutylammomium bromide in water; acetone

T=20°C; Suzuki coupling; 2 h;

Botella, Luis; Najera, Carmen

Journal of Organometallic Chemistry, 2002 , vol. 663, # 1-2 p. 46 - 57 Title/Abstract

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21 %Spectr.

With dichloro(N-(diphenylphosphino)-N-isopropyl-1,1-diphenylphosphinamine) digold(I); caesium carbonate in acetonitrile

T=80°C; 18 h; Temperature; chemoselective reaction;

Levin, Mark D.; Toste, F. Dean

Angewandte Chemie - International Edition, 2014 , vol. 53, # 24 p. 6211 - 6215 Angew. Chem., 2014 , vol. 126, # 24 p. 6325 - 6329,5 Title/Abstract

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34

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Rx-ID: 9891807 Find similar reactions

98%

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With 2C2H3O2(1-)*Pd(2+)*3Na(1+)*C18H12O9PS3(3-); potassium tertbutylate; glycerol

T=100°C; Suzuki-Miyaura Coupling; 2 h; Schlenk techniqueInert atmosphere;

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Chahdoura, Faouzi; Pradel, Christian; Gomez, Montserrat

Advanced Synthesis and Catalysis, 2013 , vol. 355, # 18 p. 3648 - 3660 Title/Abstract

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93%

With potassium tert-butylate; (1,3-di(2,4,6-(CH3)3-C6H2)-imidazol-2ylidene)Pd(OAc)2 in isopropyl alcohol

T=20°C; Suzuki-Miyaura coupling; 2 h;

Singh, Rohit; Viciu, Mihai S.; Kramareva, Natalia; Navarro, Oscar; Nolan, Steven P.

Organic Letters, 2005 , vol. 7, # 9 p. 1829 - 1832 Title/Abstract

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90%

With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate in toluene

T=110°C; Suzuki-Miyaura coupling; 15 h; Inert atmosphere;

Gerbino, Dario C.; Mandolesi, Sandra D.; Schmalz, Hans-Guenther; Podesta, Julio C.

European Journal of Organic Chemistry, 2009 , # 23 p. 3964 - 3972 Title/Abstract

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80%

With water; palladium diacetate; potassium carbonate in toluene

T=90°C; 3 h; regioselective reaction;

Scrivanti, Alberto; Beghetto, Valentina; Bertoldini, Matteo; Matteoli, Ugo

European Journal of Organic Chemistry, 2012 , # 2 p. 264 - 268 Title/Abstract

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44 %Spectr.

With dichloro(N-(diphenylphosphino)-N-isopropyl-1,1-diphenylphosphinamine) digold(I); potassium carbonate in acetonitrile

T=65°C; 18 h; Reagent/catalystTemperatureSolvent; chemoselective reaction;

Levin, Mark D.; Toste, F. Dean

Angewandte Chemie - International Edition, 2014 , vol. 53, # 24 p. 6211 - 6215 Angew. Chem., 2014 , vol. 126, # 24 p. 6325 - 6329,5 Title/Abstract

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A

B

C

D

E

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A

B

C

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35

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Rx-ID: 37305887 Find similar reactions

A: 10.5 %Chromat.

B: 5.9 %Chromat.

C: 0.9 %Chromat.

D: 17.1 %Chromat.

E: 1.2 %Chromat.

With trans-di(μ-acetato)bis[o-(di-otolylphosphino)benzyl]dipalladium(II); potassium carbonate; tris-(otolyl)phosphine in methanol; N,N-dimethyl acetamide

T=90°C; 24 h; Schlenk techniqueInert atmosphere; Catalytic behavior; Concentration;

Hartog, Tim Den; Toro, Juan Manuel Sarria; Chen, Peter

Organic Letters, 2014 , vol. 16, # 4 p. 1100 - 1103 Title/Abstract

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36

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A: 43 %Chromat.

B: 81 %Chromat.

C: 12 %Chromat.

Stage #1: 1-phenyl-1H-pyrazole; phenyl-magnesium bromide With ZnCl2N,N,N′,N′-tetramethylethylenediamine in tetrahydrofuran

T=0°C; 0.05 h; Schlenk techniqueInert atmosphere; Stage #2: 3-phenoxy-1-propene With iron (III) acetylacetonate; bathophenanthroline in tetrahydrofuran

T=0°C; 16 h; Schlenk techniqueInert atmosphere;

Asako, Sobi; Norinder, Jakob; Ilies, Laurean; Yoshikai, Naohiko; Nakamura, Eiichi

Advanced Synthesis and Catalysis, 2014 , vol. 356, # 7 p. 1481 - 1485 Title/Abstract

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A: 29 %Chromat.

B: 34 %Chromat.

C: 70 %Chromat.

Stage #1: 1-phenyl-1H-pyrazole; phenyl-magnesium bromide With ZnCl2N,N,N′,N′-tetramethylethylenediamine in tetrahydrofuran

T=0°C; 0.05 h; Schlenk techniqueInert atmosphere; Stage #2: 3-phenoxy-1-propene With iron (III) acetylacetonate; 4-tert-butyl-2(4-tert-butyl-2-pyridyl)pyridine in tetrahydrofuran

T=0°C; 16 h; Schlenk techniqueInert atmosphere; Time;

Asako, Sobi; Norinder, Jakob; Ilies, Laurean; Yoshikai, Naohiko; Nakamura, Eiichi

Advanced Synthesis and Catalysis, 2014 , vol. 356, # 7 p. 1481 - 1485 Title/Abstract

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A: 21 %Chromat.

B: 19 %Chromat.

C: 26 %Chromat.

Stage #1: 1-phenyl-1H-pyrazole; phenyl-magnesium bromide With ZnCl2N,N,N′,N′-tetramethylethylenediamine in tetrahydrofuran

T=0°C; 0.05 h; Schlenk techniqueInert atmosphere; Stage #2: 3-phenoxy-1-propene With 4,4'-dimethyl-2,2'-bipyridine; iron (III) acetylacetonate in tetrahydrofuran

T=0°C; 16 h; Schlenk techniqueInert atmosphere; Catalytic behavior; Reagent/catalyst;

Asako, Sobi; Norinder, Jakob; Ilies, Laurean; Yoshikai, Naohiko; Nakamura, Eiichi

Advanced Synthesis and Catalysis, 2014 , vol. 356, # 7 p. 1481 - 1485 Title/Abstract

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37

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Rx-ID: 38048291 Find similar reactions

58%

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With iron (III) acetylacetonate; MgBr2(Et2O) in tetrahydrofuran

T=20°C; 1 h;

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Bedford, Robin B.; Brenner, Peter B.; Carter, Emma; Carvell, Thomas W.; Cogswell, Paul M.; Gallagher, Timothy; Harvey, Jeremy N.; Murphy, Damien M.; Neeve, Emily C.; Nunn, Joshua; Pye, Dominic R.

Chemistry - A European Journal, 2014 , vol. 20, # 26 p. 7935 - 7938 Title/Abstract

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A

B

C

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38

Synthesize Find similar Rx-ID: 38051846 Find similar reactions

A: 54% B: 23%

in acetonitrile-D3

T=65°C; 1.5 h; chemoselective reaction;

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Levin, Mark D.; Toste, F. Dean

Angewandte Chemie - International Edition, 2014 , vol. 53, # 24 p. 6211 - 6215 Angew. Chem., 2014 , vol. 126, # 24 p. 6325 - 6329,5 Title/Abstract

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A

B

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39

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Rx-ID: 38051855 Find similar reactions

A: 16 %Spectr.

B: 18 %Spectr.

With dichloro(N-(diphenylphosphino)-N-isopropyl-1,1-diphenylphosphinamine) digold(I); caesium carbonate in acetonitrile

T=65°C; 18 h; chemoselective reaction;

Levin, Mark D.; Toste, F. Dean

Angewandte Chemie - International Edition, 2014 , vol. 53, # 24 p. 6211 - 6215 Angew. Chem., 2014 , vol. 126, # 24 p. 6325 - 6329,5 Title/Abstract

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A: 66 %Spectr.

B: 9 %Spectr.

With dichloro(N-(diphenylphosphino)-N-isopropyl-1,1-diphenylphosphinamine) digold(I); caesium carbonate in acetonitrile

T=65°C; 18 h; Reagent/catalystTemperatureSolvent; chemoselective reaction;

Levin, Mark D.; Toste, F. Dean

Angewandte Chemie - International Edition, 2014 , vol. 53, # 24 p. 6211 - 6215 Angew. Chem., 2014 , vol. 126, # 24 p. 6325 - 6329,5 Title/Abstract

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A

B

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40

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Rx-ID: 38051856 Find similar reactions

A: 23 %Spectr.

B: 6 %Spectr.

With dichloro(N-(diphenylphosphino)-N-isopropyl-1,1-diphenylphosphinamine) digold(I); caesium carbonate in acetonitrile

T=65°C; 18 h; chemoselective reaction;

Levin, Mark D.; Toste, F. Dean

Angewandte Chemie - International Edition, 2014 , vol. 53, # 24 p. 6211 - 6215 Angew. Chem., 2014 , vol. 126, # 24 p. 6325 - 6329,5 Title/Abstract

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A

41

B

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Rx-ID: 38051868 Find similar reactions

A: 47 %Spectr.

B: 10 %Spectr.

With dichloro(N-(diphenylphosphino)-N-isopropyl-1,1-diphenylphosphinamine) digold(I); caesium carbonate in acetonitrile

T=65°C; 18 h; chemoselective reaction;

Synthesize Find similar

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Levin, Mark D.; Toste, F. Dean

Angewandte Chemie - International Edition, 2014 , vol. 53, # 24 p. 6211 - 6215 Angew. Chem., 2014 , vol. 126, # 24 p. 6325 - 6329,5 Title/Abstract

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A

B

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42

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Rx-ID: 38051869 Find similar reactions

A: 62 %Spectr.

B: 9 %Spectr.

With dichloro(N-(diphenylphosphino)-N-isopropyl-1,1-diphenylphosphinamine) digold(I); caesium carbonate in acetonitrile

T=65°C; 18 h; chemoselective reaction;

Levin, Mark D.; Toste, F. Dean

Angewandte Chemie - International Edition, 2014 , vol. 53, # 24 p. 6211 - 6215 Angew. Chem., 2014 , vol. 126, # 24 p. 6325 - 6329,5 Title/Abstract

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A

B

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43

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Rx-ID: 38051870 Find similar reactions

A: 35 %Spectr.

B: 15 %Spectr.

With dichloro(N-(diphenylphosphino)-N-isopropyl-1,1-diphenylphosphinamine) digold(I); caesium carbonate in acetonitrile

T=65°C; 18 h; chemoselective reaction;

Levin, Mark D.; Toste, F. Dean

Angewandte Chemie - International Edition, 2014 , vol. 53, # 24 p. 6211 - 6215 Angew. Chem., 2014 , vol. 126, # 24 p. 6325 - 6329,5 Title/Abstract

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A

44

B

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Rx-ID: 38051871 Find similar reactions

A: 33 %Spectr.

B: 12 %Spectr.

With dichloro(N-(diphenylphosphino)-N-isopropyl-1,1-diphenylphosphinamine) digold(I); caesium carbonate in acetonitrile

T=65°C; 18 h; chemoselective reaction;

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Levin, Mark D.; Toste, F. Dean

Angewandte Chemie - International Edition, 2014 , vol. 53, # 24 p. 6211 - 6215 Angew. Chem., 2014 , vol. 126, # 24 p. 6325 - 6329,5 Title/Abstract

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45

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Multi-step reaction with 2 steps 1.1: tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; C69H56N2O2*BF4(1-)*H(1+) / tetrahydrofuran / 0.17 h / 20 °C / |Inert atmosphere 1.2: 0.5 h / 20 °C / |Inert atmosphere 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.25 h / 20 °C / |Inert atmosphere View Scheme

Rx-ID: 39062474 Find similar reactions

Miller, Zachary D.; Montgomery, John

Organic Letters, 2014 , vol. 16, # 20 p. 5486 - 5489 Title/Abstract

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46

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With tetrabutyl ammonium fluoride in tetrahydrofuran

T=20°C; 0.25 h; Inert atmosphere; regioselective reaction;

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Rx-ID: 39062514 Find similar reactions

Miller, Zachary D.; Montgomery, John

Organic Letters, 2014 , vol. 16, # 20 p. 5486 - 5489 Title/Abstract

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47

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Rx-ID: 39111967 Find similar reactions

30 %Spectr.

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With 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride; palladium diacetate in tetrahydrofuran; 1,4-dioxane

T=100°C; Hiyama Coupling; 24 h; Schlenk techniqueInert atmosphere; Hide Experimental Procedure

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Zhang, Pengbo; Xu, Jian; Gao, Yuzhen; Li, Xueqin; Tang, Guo; Zhao, Yufen

Synlett, 2014 , vol. 25, # 20 art. no. ST-2014-U0710-L, p. 2928 - 2932 Title/Abstract

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Hiyama Cross-Coupling; General Procedure:

General procedure: An oven dried Schlenk tube with Pd(OAc)2 (5 molpercent) and dppp (10 molpercent) was evacuated and purged with argon three times. A mixture of TBAF (1 M in THF, 0.36 mL), 2a (0.45 mmol), and benzylic phosphate (1a; 0.30 mmol) was dissolved in freshly distilled 1,4-dioxane (1.0 mL), and added at r.t. The reaction mixture was heated with stirring at 100 °C for 24 h, then cooled to ambient temperature and transferred to around-bottom flask. Silica gel (2.0 g) was added and the solvent was removed under reduced pressure to afford a free flowing powder. The powder was then dry-loaded onto a silica gel column and purified by flash chromatography using petroleum as the eluent to give the desired product 3aa.

48

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Multi-step reaction with 2 steps 1: triethylamine; 4-(N,N-dimethlyamino)pyridine / tetrahydrofuran / 16 h / 20 °C 2: palladium diacetate; 1,3-bis-(diphenylphosphino)propane; tetrabutyl ammonium fluoride / tetrahydrofuran; 1,4-dioxane / 24 h / 100 °C / |Schlenk technique; |Inert atmosphere View Scheme

Rx-ID: 39112002 Find similar reactions

Zhang, Pengbo; Xu, Jian; Gao, Yuzhen; Li, Xueqin; Tang, Guo; Zhao, Yufen

Synlett, 2014 , vol. 25, # 20 art. no. ST-2014-U0710-L, p. 2928 - 2932 Title/Abstract

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49

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Rx-ID: 32026280 Find similar reactions

99%

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Stage #1: bromobenzene With iodine; magnesium in diethyl ether

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Taber, Douglass F.; Paquette, Craig M.; Gu, Peiming; Tian, Weiwei

Inert atmosphereReflux; Stage #2: allyl bromide in diethyl ether

T=0 - 20°C; 2.08333 h; Inert atmosphere;

Journal of Organic Chemistry, 2013 , vol. 78, # 19 p. 9772 - 9780 Title/Abstract

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Stage #1: bromobenzene With magnesium in tetrahydrofuran

Chen, Huoji; Cai, Congbi; Liu, Xiaohang; Li, Xianwei; Jiang, Huanfeng

Chemical Communications, 2011 , vol. 47, # 44 p. 12224 - 12226 Title/Abstract

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Stage #2: allyl bromide in tetrahydrofuran

Stage #3: With ammonium chloride in water

With magnesium in tetrahydrofuran

T=20°C;

Uchiro, Hiromi; Shionozaki, Nobuhiro; Kobayakawa, Yu; Nakagawa, Hiroko; Makino, Kimiko

Bioorganic and Medicinal Chemistry Letters, 2012 , vol. 22, # 14 p. 4765 - 4768 Title/Abstract

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50

Synthesize Find similar Rx-ID: 34661778 Find similar reactions

With maleic anhydride; formic acid; para-xylene; [Pd(1,3-bis(2,4,6trimethylphenyl)-1,3-diazepan-2-ylidene)(dvtms)]; triethylamine in acetonitrile

T=80°C; 24 h; Inert atmosphereSchlenk techniqueReflux; Catalytic behavior; Reagent/catalyst; chemoselective reaction;

Hauwert, Peter; Dunsford, Jay J.; Tromp, Dorette S.; Weigand, Jan J.; Lutz, Martin; Cavell, Kingsley J.; Elsevier, Cornelis J.

Organometallics, 2013 , vol. 32, # 1 p. 131 - 140 Title/Abstract

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A

B

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51

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Rx-ID: 35059642 Find similar reactions

A: 20% B: 24%

Stage #1: 1-allyl-4-bromobenzene With iron (III) acetylacetonate; 2,4,6trimethylphenyl iodide; 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene in tetrahydrofuran

T=20°C; 0.5 h; Inert atmosphere; Stage #2: phenyl-magnesium bromide in tetrahydrofuran

T=0°C; 0.5 h; Inert atmosphere;

A

Sekine, Masaki; Ilies, Laurean; Nakamura, Eiichi

Organic Letters, 2013 , vol. 15, # 3 p. 714 - 717 Title/Abstract

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B

C

D

52

Synthesize Find similar Rx-ID: 35145780 Find similar reactions

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With oxygen in neat (no solvent) T=160°C; P=760.051 Torr; 1 h;

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Qi, Ben; Wang, Yanbing; Lou, Lan-Lan; Huang, Linyue; Yang, Ying; Liu, Shuangxi

Journal of Molecular Catalysis A: Chemical, 2013 , vol. 370, p. 95 - 103 Title/Abstract

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A

B

C

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53

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Rx-ID: 35357766 Find similar reactions

A: 12 %Chromat.

B: 75 %Chromat.

C: 9 %Chromat.

Stage #1: 2-(1,3-dioxolan-2-yl)ethylMgBr With ferrous acetate; 1,3-bis(2,4,6trimethylphenyl)imidazolinium chloride in tetrahydrofuran

T=50 - 60°C; Kumada Cross-Coupling; 0.333333 h; Schlenk techniqueInert atmosphere; Stage #2: (3-iodoprop-1-yl)benzene in tetrahydrofuran

T=20°C; Kumada Cross-Coupling; 24 h; Schlenk techniqueInert atmosphere;

Guisan-Ceinos, Manuel; Tato, Francisco; Bunuel, Elena; Calle, Paloma; Cardenas, Diego J.

Chemical Science, 2013 , vol. 4, # 3 p. 1098 - 1104 Title/Abstract

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54

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Rx-ID: 35564420 Find similar reactions

42 %Spectr.

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With [Ru(tris(2,2'-bipyridyl))3]Cl2·6H2O; N-ethyl-N,N-diisopropylamine in acetonitrile-D3

15 h; Inert atmosphereIrradiation;

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Donck, Simon; Baroudi, Abdulkader; Fensterbank, Louis; Goddard, Jean-Philippe; Ollivier, Cyril

Advanced Synthesis and Catalysis, 2013 , vol. 355, # 8 p. 1477 - 1482 Title/Abstract

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A

B

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55

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Rx-ID: 36343797 Find similar reactions

Erdik, Ender; Eroglu, Fatma; Kalkan, Melike; Pekel, Oezgen Oemuer; Oezkan, Duygu; Serdar, Ebru Z.

Journal of Organometallic Chemistry, 2013 , vol. 745-746, p. 235 - 241 Title/Abstract

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in tetrahydrofuran

T=25°C; 0.5 h; Inert atmosphere; Solvent; Overall yield = 99 percentChromat.;

56

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Rx-ID: 36343798 Find similar reactions

20 %Chromat.

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Erdik, Ender; Eroglu, Fatma; Kalkan, Melike; Pekel, Oezgen Oemuer; Oezkan, Duygu; Serdar, Ebru Z.

Journal of Organometallic Chemistry, 2013 , vol. 745-746, p. 235 - 241 Title/Abstract

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in tetrahydrofuran

T=25°C; 0.5 h; Inert atmosphere;

A

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57

Synthesize Find similar Rx-ID: 36381194 Find similar reactions

With samarium diiodide; tert-butyl alcohol in tetrahydrofuran

T=-78 - 20°C; Inert atmosphere; Hide Experimental Procedure

Schaefer, Sara L.; Roberts, Connor L.; Volz, Erasmus O.; Grasso, Monika R.; O'Neil, Gregory W.

Tetrahedron Letters, 2013 , vol. 54, # 45 p. 6125 - 6128 Title/Abstract

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Alkene 28

General procedure: To a freshly prepared solution of SmI2 (0.1 M, 10.2 mL) at -78 °C was added degassed tBuOH(290 μL, 3.06 mmol) and the mixture was warmed to 0 °C for 10 min. The solution was cooledto -78 °C before adding 26 (0.050 g, 0.14) and the mixture was then warmed to roomtemperature for 1 h. The reaction was quenched with aq. NH4Cl (25 mL) and extracted with ethylacetate (2 x 15 mL). The combined organic extracts were dried over MgSO4 and concentrated in vacuo. Purification by flash column chromatography on silica (20:1 hexanes:ethyl acetate)afforded 28 (21 mg, 66percent). IR (neat) 2955, 2928, 2856, 1737, 1716, 1590, 1562, 1472, 1437 cm-1. 1H NMR (500 MHz, CDCl3): δ 7.37 (d, J = 1.6 Hz, 1H), 7.08 (dd, J = 8.3, 1.6 Hz, 1H), 6.83(d, J = 8.3 Hz, 1H), 5.92 (m, 1H), 5.08 (s, 1H), 5.06 (dd, J = 6.7, 1.2 Hz, 1H), 3.87 (s, 3H), 3.30(d, J = 6.6 Hz, 2H). 13C NMR (126 MHz, CDCl3): δ 154.4, 137.0, 133.4, 130.4, 128.5, 125.9,116.1, 111.8, 56.3, 38.7.

A

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58

Synthesize Find similar Rx-ID: 36381196 Find similar reactions

With samarium diiodide; tert-butyl alcohol in tetrahydrofuran

T=-78 - 20°C; Inert atmosphere; Hide Experimental Procedure

Schaefer, Sara L.; Roberts, Connor L.; Volz, Erasmus O.; Grasso, Monika R.; O'Neil, Gregory W.

Tetrahedron Letters, 2013 , vol. 54, # 45 p. 6125 - 6128 Title/Abstract

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Alkene 28

General procedure: To a freshly prepared solution of SmI2 (0.1 M, 10.2 mL) at -78 °C was added degassed tBuOH(290 μL, 3.06 mmol) and the mixture was warmed to 0 °C for 10 min. The solution was cooledto -78 °C before adding 26 (0.050 g, 0.14) and the mixture was then warmed to roomtemperature for 1 h. The reaction was quenched with aq. NH4Cl (25 mL) and extracted with ethylacetate (2 x 15 mL). The combined organic extracts were dried over MgSO4 and concentrated in vacuo. Purification by flash column chromatography on silica (20:1 hexanes:ethyl acetate)afforded 28 (21 mg, 66percent). IR (neat) 2955, 2928, 2856, 1737, 1716, 1590, 1562, 1472, 1437 cm-1. 1H NMR (500 MHz, CDCl3): δ 7.37 (d, J = 1.6 Hz, 1H), 7.08 (dd, J = 8.3, 1.6 Hz, 1H), 6.83(d, J = 8.3 Hz, 1H), 5.92 (m, 1H), 5.08 (s, 1H), 5.06 (dd, J = 6.7, 1.2 Hz, 1H), 3.87 (s, 3H), 3.30(d, J = 6.6 Hz, 2H). 13C NMR (126 MHz, CDCl3): δ 154.4, 137.0, 133.4, 130.4, 128.5, 125.9,116.1, 111.8, 56.3, 38.7.

A

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59

Synthesize Find similar Rx-ID: 36890544 Find similar reactions

B: 76%

60

With [Cu(2,9-dimethyl-1,10-phenanthroline)2]*-[HF2]− in acetonitrile

T=110°C; 15 h; Schlenk techniqueInert atmosphere; Reagent/catalystTimeSolvent;

Liu, Yanpin; Chen, Chaohuang; Li, Huaifeng; Huang, Kuo-Wei; Tan, Jianwei; Weng, Zhiqiang

Organometallics, 2013 , vol. 32, # 21 p. 6587 - 6592 Title/Abstract

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Rx-ID: 14878117 Find similar reactions

Multi-step reaction with 2 steps 1: 41 percent Chromat. / Mg / 600 °C / 0.01 - 0.1 Torr 2: 14 percent Chromat. / Mg / 600 °C / 0.01 - 0.1 Torr View Scheme

Aitken, R. Alan; Hodgson, Philip K.G.; Morrison, John J.; Oyewale, Adebayo O.

Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 3 p. 402 - 415 Title/Abstract

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100 %Chromat.

With Pd(P(t-Bu)2Me)2; potassium tert-butylate; N,N-dicyclohexylamine in 1,4dioxane

T=20°C; 24 h; Inert atmosphere;

Bissember, Alex C.; Levina, Anna; Fu, Gregory C.

Journal of the American Chemical Society, 2012 , vol. 134, # 34 p. 14232 - 14237 Title/Abstract

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61

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With tetrabutyl ammonium fluoride; water

Rx-ID: 32808605 Find similar reactions

Taylor, Peter G.; Bassindale, Alan R.; El Aziz, Youssef; Pourny, Manuel; Stevenson, Richard; Hursthouse, Michael B.; Coles, Simon J.

Dalton Transactions, 2012 , vol. 41, # 7 p. 2048 - 2059 Title/Abstract

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A

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62

Synthesize Find similar Rx-ID: 33482870 Find similar reactions

Multi-step reaction with 2 steps 1: pyridine 2: hydrogen / toluene / 16 h / 60 °C View Scheme

Noujima, Akifumi; Mitsudome, Takato; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi

Chemical Communications, 2012 , vol. 48, # 53 p. 6723 - 6725 Title/Abstract

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A

B

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63

Synthesize Find similar Rx-ID: 33482877 Find similar reactions

A: 89% B: 10%

With hydrotalcite-supported Au nanoparticles in toluene

T=80°C; 3 h; Inert atmosphere; chemoselective reaction;

Noujima, Akifumi; Mitsudome, Takato; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi

Chemical Communications, 2012 , vol. 48, # 53 p. 6723 - 6725 Title/Abstract

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A

B

C

D

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64

Synthesize Find similar Rx-ID: 33482878 Find similar reactions

With hydrogen in toluene

T=80°C; P=760.051 Torr; 12 h; chemoselective reaction;

Noujima, Akifumi; Mitsudome, Takato; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi

Chemical Communications, 2012 , vol. 48, # 53 p. 6723 - 6725 Title/Abstract

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A

B

C

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65

Synthesize Find similar Rx-ID: 33482879 Find similar reactions

With hydrogen in toluene

T=80°C; P=760.051 Torr; 12 h; chemoselective reaction;

Noujima, Akifumi; Mitsudome, Takato; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi

Chemical Communications, 2012 , vol. 48, # 53 p. 6723 - 6725

Title/Abstract

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A

B

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66

Synthesize Find similar Rx-ID: 33482888 Find similar reactions

With hydrogen in toluene

T=60°C; 16 h; chemoselective reaction;

Noujima, Akifumi; Mitsudome, Takato; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi

Chemical Communications, 2012 , vol. 48, # 53 p. 6723 - 6725 Title/Abstract

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A

B

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67

Synthesize Find similar Rx-ID: 33482890 Find similar reactions

Multi-step reaction with 2 steps 1: pyridine 2: hydrotalcite-supported Au nanoparticles / toluene / 3 h / 80 °C / Inert atmosphere View Scheme

Noujima, Akifumi; Mitsudome, Takato; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi

Chemical Communications, 2012 , vol. 48, # 53 p. 6723 - 6725 Title/Abstract

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A

B

C

D

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68

Synthesize Find similar Rx-ID: 33482891 Find similar reactions

Multi-step reaction with 2 steps 1: pyridine 2: hydrogen / toluene / 12 h / 80 °C / 760.05 Torr View Scheme

Noujima, Akifumi; Mitsudome, Takato; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi

Chemical Communications, 2012 , vol. 48, # 53 p. 6723 - 6725 Title/Abstract

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A

B

C

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69

Synthesize Find similar Rx-ID: 33482892 Find similar reactions

Multi-step reaction with 2 steps 1: pyridine 2: hydrogen / toluene / 12 h / 80 °C / 760.05 Torr View Scheme

Noujima, Akifumi; Mitsudome, Takato; Mizugaki, Tomoo; Jitsukawa, Koichiro; Kaneda, Kiyotomi

Chemical Communications, 2012 , vol. 48, # 53 p. 6723 - 6725 Title/Abstract

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A

B

C

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70

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Rx-ID: 33998746 Find similar reactions

With PEPPSI-IPr catalyst in tetrahydrofuran; 1,3-dimethyl-imidazolidin-2-one

Negishi coupling reaction; 0.5 h; Inert atmosphere;

McCann, Lucas C.; Hunter, Howard N.; Clyburne, Jason A. C.; Organ, Michael G.

Angewandte Chemie - International Edition, 2012 , vol. 51, # 28 p. 7024 - 7027 Title/Abstract

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71

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Rx-ID: 34081036 Find similar reactions

96%

With Pd(P(t-Bu)2Me)2; potassium tert-butylate; N,N-dicyclohexylamine in 1,4dioxane

T=80°C; 8 h; Inert atmosphere;

Bissember, Alex C.; Levina, Anna; Fu, Gregory C.

Journal of the American Chemical Society, 2012 , vol. 134, # 34 p. 14232 - 14237 Title/Abstract

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A

B

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72

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Rx-ID: 34200587 Find similar reactions

A: 67.6% B: 17%

With C31H37ClN3NiO2(1-)*Li(1+) in tetrahydrofuran

T=25°C; 0.333333 h; Inert atmosphere; Overall yield = 85.2percent; Hide Experimental Procedure

Gartia, Yashraj; Nasini, Udaya Bhasker; Ghosh, Anindya; Biswas, Abhijit; Stadler, Matthew

Journal of Molecular Catalysis A: Chemical, 2012 , vol. 363-364, p. 322 - 327,6 Title/Abstract

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2.4 Cross coupling of CH2Cl2 with butylmagnesium chloride

General procedure: Cross-coupling reactions of Grignard reagents with CH2Cl2 were performed according to the following general method. Catalyst 2 (1.0 mg, 1.74 μmol) in 1.0 mL THF was added using a gas-tight syringe to a 5 mL round bottom flask purged with N2. To this solution, 2 M n-butylmagnesium chloride in THF (0.42 mL, 0.84 mmol) was added. CH2Cl2 (27 μL, 0.42 mmol) in 2 mL THF was added to the reaction mixture. Samples were collected for analysis after 20 min. At the end of the reaction, excess Grignard reagent was destroyed using methanol and the reaction products were analyzed by GC–MS using an internal standard to quantify product formation.

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73

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74

With C31H37ClFeN3O2 in tetrahydrofuran

T=25°C; 0.0833333 h; Inert atmosphere;

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Gartia, Yashraj; Pulla, Sharon; Ramidi, Punnamchandar; Farris, Carolina Costa; Nima, Zeid; Jones, Darin E.; Biris, Alexandru S.; Ghosh, Anindya

Catalysis Letters, 2012 , vol. 142, # 11 p. 1397 - 1404 Title/Abstract

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Rx-ID: 34547968 Find similar reactions

55%

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With bis(η3-allyl-μ-chloropalladium(II)) in tetrahydrofuran

T=50°C; Stille Cross Coupling; 7 h; Inert atmosphere;

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Martinez-Arranz, Sheila; Carrera, Nora; Albeniz, Ana C.; Espinet, Pablo; Vidal-Moya, Alejandro

Advanced Synthesis and Catalysis, 2012 , vol. 354, # 18 p. 3551 - 3560 Title/Abstract

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75

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Rx-ID: 30188389 Find similar reactions

13%

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With C20H14Cl5FeN2O2 in diethyl ether

T=20°C;

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Reckling, Amy M.; Martin, Dana; Dawe, Louise N.; Decken, Andreas; Kozak, Christopher M.

Journal of Organometallic Chemistry, 2011 , vol. 696, # 3 p. 787 - 794 Title/Abstract

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76

Synthesize Find similar Rx-ID: 30644534 Find similar reactions

With triethanolamine; C53H75CoN4O14(1+)*ClO4(1-); rose bengal disodium salt in acetonitrile

T=20°C; 12 h; Inert atmosphereVisible light irradiation;

Tahara, Keishiro; Hisaeda, Yoshio

Green Chemistry, 2011 , vol. 13, # 3 p. 558 - 561 Title/Abstract

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77

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Rx-ID: 30644535 Find similar reactions

With triethanolamine; C53H75CoN4O14(1+)*ClO4(1-); rose bengal disodium salt in acetonitrile

T=20°C; 12 h; Inert atmosphereVisible light irradiation;

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Tahara, Keishiro; Hisaeda, Yoshio

Green Chemistry, 2011 , vol. 13, # 3 p. 558 - 561 Title/Abstract

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C

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78

Synthesize Find similar Rx-ID: 31726176 Find similar reactions

A: 6 %Spectr.

B: 12 %Spectr.

C: 16 %Spectr.

With phloroglucinol trimethyl ether; [Nb(CO)2(NtBu)(CH(C(Me)N(2,6diisopropylphenyl))2)]; hydrogen in benzene-d6

T=20°C; 2 h;

Gianetti, Thomas L.; Tomson, Neil C.; Arnold, John; Bergman, Robert G.

Journal of the American Chemical Society, 2011 , vol. 133, # 38 p. 14904 - 14907 Title/Abstract

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D

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79

Synthesize Find similar Rx-ID: 31881032 Find similar reactions

80

in toluene

T=20°C; 1.25 h;

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Palacios, Laura; Miao, Xiaowei; Di Giuseppe, Andrea; Pascal, Simon; Cunchillos, Carmen; Castarlenas, Ricardo; Perez-Torrente, Jesus J.; Lahoz, Fernando J.; Dixneuf, Pierre H.; Oro, Luis A.

Organometallics, 2011 , vol. 30, # 19 p. 5208 - 5213 Title/Abstract

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Rx-ID: 32067380 Find similar reactions

99 %Chromat.

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With bis(1,5-cyclooctadiene)nickel (0); triethylsilyl trifluoromethanesulphonate; triethylamine; diphenylcyclohexyl phosphine in toluene

T=20°C; Heck type reaction; P=760.051 Torr; 2 h;

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Matsubara, Ryosuke; Gutierrez, Alicia C.; Jamison, Timothy F.

Journal of the American Chemical Society, 2011 , vol. 133, # 47 p. 19020 - 19023 Title/Abstract

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81

Synthesize Find similar Rx-ID: 29279792 Find similar reactions

Al-Etaibi, Alya M.; Al-Awadi, Nouria A.; Ibrahim, Maher R.; Ibrahim, Yehia A.

Molecules, 2010 , vol. 15, # 1 p. 407 - 419 Title/Abstract

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T=600°C; P=0.01 Torr;

82

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Rx-ID: 29315567 Find similar reactions

90%

With cesium fluoride in ethanol; water

T=50°C; Stille coupling; 5 h; Inert atmosphere;

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Jin, Myung-Jong; Lee, Dong-Hwan

Angewandte Chemie - International Edition, 2010 , vol. 49, # 6 p. 1119 - 1122 Title/Abstract

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90%

With C20H34NO2PPd; cesium fluoride in tetrahydrofuran

T=20°C; Stille coupling; 6 h; Inert atmosphere;

Lee, Dong-Hwan; Taher, Abu; Ahn, Wha-Seung; Jin, Myung-Jong

Chemical Communications, 2010 , vol. 46, # 3 p. 478 - 480 Title/Abstract

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83

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Rx-ID: 29315811 Find similar reactions

A: 7% B: 77%

Cadierno, Victorio; Francos, Javier; Gimeno, Jose

Green Chemistry, 2010 , vol. 12, # 1 p. 135 - 143 Title/Abstract

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With RuCl2(η-C6H6)(TPPMS) in water

T=100°C; 3 h; Inert atmosphere;

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B

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84

Synthesize Find similar Rx-ID: 29645345 Find similar reactions

A: 95%

Stage #1: With Dess-Martin periodane in dichloromethane

T=20°C; Stage #2: With water; sodium carbonate

T=20°C;

Andreou, Thanos; Bures, Jordi; Vilarrasa, Jaume

Tetrahedron Letters, 2010 , vol. 51, # 14 p. 1863 - 1866 Title/Abstract

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85

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A: 100% B: 100%

With 3-chloro-benzenecarboperoxoic acid in chloroform-d1

T=20°C;

Andreou, Thanos; Bures, Jordi; Vilarrasa, Jaume

Tetrahedron Letters, 2010 , vol. 51, # 14 p. 1863 - 1866 Title/Abstract

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C

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86

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Rx-ID: 29754874 Find similar reactions

Lazzaroni, Simone; Protti, Stefano; Fagnoni, Maurizio; Albini, Angelo

Journal of Photochemistry and Photobiology A: Chemistry, 2010 , vol. 210, # 2-3 p. 140 - 144 Title/Abstract

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Photolysis;

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87

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Rx-ID: 29754879 Find similar reactions

Lazzaroni, Simone; Protti, Stefano; Fagnoni, Maurizio; Albini, Angelo

Journal of Photochemistry and Photobiology A: Chemistry, 2010 , vol. 210, # 2-3 p. 140 - 144 Title/Abstract

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in methanol

Photolysis;

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88

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C: 0.18 g

Stage #1: cinnamyl bromide With indium in tetrahydrofuran

T=20°C; 0.5 h; Inert atmosphere; Stage #2: 1,1-Diphenylmethanol in tetrahydrofuran

T=20°C; 0.5 h; Inert atmosphere;

Yasuda, Makoto; Haga, Masahiko; Nagaoka, Yasunori; Baba, Akio

European Journal of Organic Chemistry, 2010 , # 28 p. 5359 - 5363 Title/Abstract

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89

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Rx-ID: 29855372 Find similar reactions

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With sodium hydroxide in water

T=100°C; Suzuki coupling; 4 h;

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Li, Yang; Fan, Xiaobin; Qi, Junjie; Ji, Junyi; Wang, Shulan; Zhang, Guoliang; Zhang, Fengbao

Materials Research Bulletin, 2010 , vol. 45, # 10 p. 1413 - 1418 Title/Abstract

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90

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91

With C34H43Cl2N3O2Pd; n-butyl zinc bromide; lithium bromide in tetrahydrofuran; 1,3-dimethyl-imidazolidin-2-one

T=20°C; 24 h; Inert atmosphere;

Nasielski, Joanna; Hadei, Nilofaur; Achonduh, George; Kantchev, Eric Assen B.; O'Brien, Christopher J.; Lough, Alan; Organ, Michael G.

Chemistry - A European Journal, 2010 , vol. 16, # 35 p. 10844 - 10853 Title/Abstract

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With C24H30Cl3N3Pd; n-butyl zinc bromide; lithium bromide in tetrahydrofuran; 1,3-dimethyl-imidazolidin-2-one

T=20°C; 24 h; Inert atmosphere;

Nasielski, Joanna; Hadei, Nilofaur; Achonduh, George; Kantchev, Eric Assen B.; O'Brien, Christopher J.; Lough, Alan; Organ, Michael G.

Chemistry - A European Journal, 2010 , vol. 16, # 35 p. 10844 - 10853 Title/Abstract

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Rx-ID: 29912375 Find similar reactions

48%

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GRUeNENTHAL GMBH; FRANK, Robert; BAHRENBERG, Gregor; CHRISTOPH, Thomas; SCHIENE, Klaus; DE VRY, Jean; DAMANN, Nils; FRORMANN, Sven; LESCH, Bernhard; LEE, Jeewoo; KIM, Yong-Soo; KIM, Myeong-Seop

Patent: WO2010/127855 A1, 2010 ; Location in patent: Page/Page column 142; 143 ;

in tetrahydrofuran

T=10 - 20°C; Hide Experimental Procedure

Title/Abstract

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6.6.21.a:

To a stirred solution of allyl chloride (5g, 0.065 mol) in tetrahydrofuran (50 mL) phenylmagnesium bromide (1 M, 54 mL) was added dropwise at 10-15 0C. The resulting reaction mixture was stirred at ambient temperature for 2 hours. TLC (hexane, Rf= 0.8) showed complete consumption of starting material. The reaction mixture was quenched with saturated solution of ammonium chloride (50 mL) and the aqueous part was extracted with hexane (3 x 50 mL). The combined organic layer was washed with brine (100 mL) and dried over anhydrous magnesium sulfate. The organic part was concentrated under reduced pressure followed by fractional distillation process to afford pure compound (3.8 g, 48 percent yield).

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92

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With hydrogen in hexane

T=20°C; P=15001.5 Torr; Autoclave;

Leitmannova, Eliska; Jirasek, Petr; Rak, Jakub; Potucka, Lucie; Kacer, Petr; Cerveny, Libor

Research on Chemical Intermediates, 2010 , vol. 36, # 5 p. 511 - 522 Title/Abstract

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93

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Rx-ID: 1763938 Find similar reactions

41%

With para-dicyanobenzene; 2,4,6-trimethyl-pyridine; biphenyl in acetonitrile

T=10°C; Irradiation;

Arnold, Donald R.; Mines, Shelley A.

Canadian Journal of Chemistry, 1989 , vol. 67, p. 689 - 698 Title/Abstract

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41%

With para-dicyanobenzene; 2,4,6-trimethyl-pyridine; biphenyl in acetonitrile

T=10°C; Irradiationseveral alkenes investigated; Mechanism;

Arnold, Donald R.; Mines, Shelley A.

Canadian Journal of Chemistry, 1989 , vol. 67, p. 689 - 698 Title/Abstract

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14 % Chromat.

With magnesium

T=600°C; P=0.01 - 0.1 Torr;

Aitken, R. Alan; Hodgson, Philip K.G.; Morrison, John J.; Oyewale, Adebayo O.

Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 3 p. 402 - 415 Title/Abstract

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Hide Details

With hydrogen

Bavykin, Dmitry V.; Walsh, Frank C.

European Journal of Inorganic Chemistry, 2009 , # 8 p. 977 - 997 Title/Abstract

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94

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Rx-ID: 9594747 Find similar reactions

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95%

With dichloro bis(acetonitrile) palladium(II); 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene in tetrahydrofuran

T=20°C; Kumada-Corriu reaction; 14 h; Inert atmosphere;

Lopez-Perez, Ana; Adrio, Javier; Carretero, Juan C.

Organic Letters, 2009 , vol. 11, # 23 p. 5514 - 5517 Title/Abstract

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82%

Stage #1: vinyl-magnesium bromide With indium(III) chloride in tetrahydrofuran

Lee, Phil Ho; Lee, Sung Wook; Seomoon, Dong

Organic Letters, 2003 , vol. 5, # 26 p. 4963 - 4966 Title/Abstract

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Stage #2: benzyl bromide With tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran

Heating;

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95

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A: 1% B: 99%

With tetra-n-butylammonium tetrafluoroborate in N,N-dimethyl-formamide

Electrochemical reactionInert atmosphere;

A

Poizot, Philippe; Jouikov, Viatcheslav; Simonet, Jacques

Tetrahedron Letters, 2009 , vol. 50, # 7 p. 822 - 824 Title/Abstract

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B

C

96

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Rx-ID: 28388152 Find similar reactions

A: 15% B: 30% C: 55%

With niobium pentachloride; zinc in tetrahydrofuran; benzene

T=23°C; 3 h; Inert atmosphere;

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Oh, Kyungsoo; Knabe, William Eric

Tetrahedron, 2009 , vol. 65, # 15 p. 2966 - 2974 Title/Abstract

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97

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Rx-ID: 28496445 Find similar reactions

86%

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With potassium hydroxide; 2C8H8NO2(1-)*2Cl(1-)*2Pd(2+); tetrabutylammomium bromide in water; acetone

T=50°C; Suzuki-Miyaura coupling; 4.5 h;

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Alacid, Emilio; Najera, Carmen

Journal of Organic Chemistry, 2009 , vol. 74, # 6 p. 2321 - 2327 Title/Abstract

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98

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Rx-ID: 28697734 Find similar reactions

66%

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With potassium hydroxide; tetrabutylammomium bromide in water; acetone

T=50°C; 8 h;

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Alacid, Emilio; Najera, Carmen

Journal of Organometallic Chemistry, 2009 , vol. 694, # 11 p. 1658 - 1665 Title/Abstract

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A

B

C

99

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Rx-ID: 28841995 Find similar reactions

C: 21.3 %Chromat.

With C24H25Cl3N3Pd; lithium bromide in tetrahydrofuran; 10,11-dihydro-5-[3(methylamino)propyl]-5H-dibenz(b,f)azepin

T=20°C; Negishi coupling reaction; 2 h; Inert atmosphere;

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Chass, Gregory A.; O'Brien, Christopher J.; Hadei, Niloufar; Kantchev, Eric Assen B.; Mu, Wei-Hua; Fang, De-Cai; Hopkinson, Alan C.; Csizmadia, Imre G.; Organ, Michael G.

Chemistry - A European Journal, 2009 , vol. 15, # 17 p. 4281 - 4288 Title/Abstract

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