4-(2-溴苯基)-1-丁烯合成路线 （共 23 条）
反应条件
sodium hydroxide; dihydrogen peroxide; dichloro(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) in tetrahydrofuran To a soln. of haloalkene is added 9-BBN at 0°C, mixt. is stirred for 5 h at room temp., catalyst and aq. NaOH are added, after refluxing for 14 h, the unreacted borane is oxidized with H2O2 for 1h.; Isolated by chromy. over silica gel with hexane-ether, identified by IR,(1)H NMR, mass spectrometry, elem. anal.;
参考文献
Miyaura, Norio; Ishiyama, Tatsuo; Sasaki, Hirotomo; Ishikawa, Masako; Satoh, Makoto; Suzuki, Akira
Journal of the American Chemical Society, 1989 , vol. 111, # 1 p. 314 - 321
反应条件
2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in benzene T=0 - 150°C;
参考文献
Abeywickrema, Anil N.; Beckwith, Athelstan L. J.
Journal of the Chemical Society, Chemical Communications, 1986 , # 6 p. 464 - 465
反应条件
sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 1.) THF, r.t., 5 h; 2.) reflux, 14 h; Yield given. Multistep reaction;
参考文献
Miyaura, Norio; Ishiyama, Tatsuo; Sasaki, Hirotomo; Ishikawa, Masako; Satoh, Makoto; Suzuki, Akira
Journal of the American Chemical Society, 1989 , vol. 111, # 1 p. 314 - 321
反应条件
1.1: 9-borabicyclo[3.3.1]nonane / hexane / 18 h / 20 °C 1.2: 82 percent / NaOH; H2O2 / tetrahydrofuran / 1.5 h / 50 °C 2.1: 58 percent / chromium trioxide; acetic acid / 18 h / 20 °C 3.1: thionyl chloride / 0.75 h / Heating 4.1: 540 mg / aluminium chloride / CS2 / 3 h / Heating View Scheme
参考文献
Ghoneim, Ola M.; Legere, Jacqueline A.; Golbraikh, Alexander; Tropsha, Alexander; Booth, Raymond G.
Bioorganic and Medicinal Chemistry, 2006 , vol. 14, # 19 p. 6640 - 6658
反应条件
hydrazine hydrate; 2-nitro-benzenesulfonyl chloride in acetonitrile T=0 - 20°C; 18 h; Inert atmosphere;
参考文献
Cho, Seung Hwan; Hartwig, John F.
Journal of the American Chemical Society, 2013 , vol. 135, # 22 p. 8157 - 8160
反应条件
bis(benzonitrile)palladium(II) dichloride; AgNO2; CuCl2·2H2O; nitromethane; oxygen; tert-butyl alcohol T=20°C; Wacker Oxidation; P=760.051 Torr; 6 h; Overall yield = 71 percent;
参考文献
Wickens, Zachary K.; Morandi, Bill; Grubbs, Robert H.
Angewandte Chemie - International Edition, 2013 , vol. 52, # 43 p. 11257 - 11260
Angew. Chem., 2013 , vol. 125, # 43 p. 11467 - 11470
反应条件
bis(benzonitrile)palladium(II) dichloride; AgNO2; CuCl2·2H2O; nitromethane; oxygen; tert-butyl alcohol T=20°C; Wacker Oxidation; P=760.051 Torr; 6 h; Overall yield = 71 percent;
参考文献
Wickens, Zachary K.; Morandi, Bill; Grubbs, Robert H.
Angewandte Chemie - International Edition, 2013 , vol. 52, # 43 p. 11257 - 11260
Angew. Chem., 2013 , vol. 125, # 43 p. 11467 - 11470
反应条件
FeF3*H2O; ethylmagnesium bromide; SIDip*HCl in tetrahydrofuran T=60°C; 80 h; Inert atmosphere;
参考文献
Journal of the American Chemical Society, , vol. 131, # 33 p. 11949 - 11963
反应条件
1: 4‑(2‑bromophenyl)‑1‑butene With n-butyllithium in tetrahydrofuran; hexane
T=-78°C; 1 h; Inert atmosphere;
2: N,N-dimethyl-formamide in tetrahydrofuran; hexane
T=-78°C; 1 h; Inert atmosphere;
3: With water in tetrahydrofuran; hexane
T=-78°C;
参考文献
Xing, Siyang; Pan, Wenyan; Liu, Chang; Ren, Jun; Wang, Zhongwen
Angewandte Chemie - International Edition, 2010 , vol. 49, # 18 p. 3215 - 3218
反应条件
1: 73 percent / 9-BBN, 6M NaOH, 30percent H2O2 / 1.5 h / 50 °C
2: 66 percent / chromium trioxide, 1.5M sulfuric acid / acetone / 4 h / 0 °C
3: thionyl chloride / 2.5 h / Ambient temperature
4: CH2Cl2 / 0.25 h / 0 °C
5: 5 percent / K2CO3, tris(dibenzylideneacetone)dipalladium(0), tri-(o-tolyl)phosphine / toluene / 25 h / 110 °C
View Scheme
参考文献
Wolfe, John P.; Rennels, Roger A.; Buchwald, Stephen L.
Tetrahedron, 1996 , vol. 52, # 21 p. 7525 - 7546
