Palladium-catalyzed C-O bond formation: direct synthesis of phenols and aryl/alkyl ethers from activated aryl halides

被引:99
作者
Chen, Guoshu
Chan, Albert S. C.
Kwong, Fuk Yee
机构
[1] Guangzhou Univ, Sch Chem & Chem Engn, Guangzhou 510402, Peoples R China
[2] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Open Lab Chirotechnol, Inst Mol Technol Drug Discovery & Synth, Kowloon, Hong Kong, Peoples R China
关键词
D O I
10.1016/j.tetlet.2006.11.036
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and efficient palladium-catalyzed carbon-oxygen bond formation is reported. The palladium-tri-tert-butylphosphine complex was found to be effective in converting haloarenes to corresponding substituted phenols. This methodology offers a direct transformation of aryl halides to phenols, as well as the straightforward application to generate a wide variety of diaryl or alkyl/aryl ethers. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:473 / 476
页数:4
相关论文
共 28 条
[1]   Novel purine nitrile derived inhibitors of the cysteine protease cathepsin K [J].
Altmann, E ;
Cowan-Jacob, SW ;
Missbach, M .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (24) :5833-5836
[2]   The selective reaction of aryl halides with KOH: Synthesis of phenols, aromatic ethers, and benzofurans [J].
Anderson, Kevin W. ;
Ikawa, Takashi ;
Tundel, Rachel E. ;
Buchwald, Stephen L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (33) :10694-10695
[3]   Significantly improved method for the Pd-catalyzed coupling of phenols with aryl halides: Understanding ligand effects [J].
Burgos, Carlos H. ;
Barder, Timothy E. ;
Huang, Xiaohua ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) :4321-4326
[4]   The nitration of electron-rich aromatics [J].
Dwyer, CL ;
Holzapfel, CW .
TETRAHEDRON, 1998, 54 (27) :7843-7848
[5]  
FRIXCHKOM H, 1982, LIEBIGS ANN CHEM, P1423
[6]   Selective and one-pot formation of phenols by anodic oxidation [J].
Fujimoto, K ;
Tokuda, Y ;
Maekawa, H ;
Matsubara, Y ;
Mizuno, T ;
Nishiguchi, I .
TETRAHEDRON, 1996, 52 (11) :3889-3896
[7]  
FYFE CA, 1971, CHEM HYDROXYL GROUP, V1
[8]   Alcohols, ethers and phenols [J].
George, T ;
Mabon, R ;
Sweeney, G ;
Sweeney, JB ;
Tavassoli, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (16) :2529-2574
[9]  
Hoarau C, 2003, SYNLETT, P127
[10]   Air stable, sterically hindered ferrocenyl dialkylphosphines for palladium-catalyzed C-C, C-N, and C-O bond-forming cross-couplings [J].
Kataoka, N ;
Shelby, Q ;
Stambuli, JP ;
Hartwig, JF .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16) :5553-5566