Regioselective copper-catalyzed chlorination and bromination of arenes with O2 as the oxidant

被引：188
作者：
Yang, Lujuan [1 ,2 ,3 ]
Lu, Zhan [1 ]
Stahl, Shannon S. [1 ]
机构：
[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA
[2] Xiamen Univ, Dept Chem, Coll Chem & Chem Engn, Xiamen 361005, Peoples R China
[3] Xiamen Univ, State Key Lab Phys Chem Solid Surfaces, Xiamen 361005, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2009年 / 42期
关键词：
C-H; AROMATIC-COMPOUNDS; MILD CONDITIONS; BOND FORMATION; COMPLEXES; OXYBROMINATION; EFFICIENT; BROMIDE; PHENOLS; KETONES;
D O I：
10.1039/b915487f
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Electron-rich aromatic C-H bonds undergo regioselective chlorination and bromination in the presence of CuX2, LiX (X = Cl, Br) and molecular oxygen. Preliminary mechanistic insights suggest that the bromination and chlorination reactions proceed by different pathways.
引用
收藏
页码：6460 / 6462
页数：3
相关论文
共 33 条
[1]   An alternative method for the regio- and stereoselective bromination of alkenes, alkynes, toluene derivatives and ketones using a bromide/bromate couple [J].
Adimurthy, Subbarayappa ;
Ghosh, Sudip ;
Patoliya, Paresh U. ;
Ramachandraiah, Gadde ;
Agrawal, Manoj ;
Gandhi, Mahesh R. ;
Upadhyay, Sumesh C. ;
Ghosh, Pushpito K. ;
Ranu, Brindaban C. .
GREEN CHEMISTRY, 2008, 10 (02) :232-237
[2]   Copper-mediated C-H bond arylation of arenes with arylboronic acids [J].
Ban, Ikuya ;
Sudo, Tomoko ;
Taniguchi, Tadashi ;
Itami, Kenichiro .
ORGANIC LETTERS, 2008, 10 (16) :3607-3609
[3]   COPPER(II) BROMIDE COMPLEXES .1. A SPECTROPHOTOMETRIC STUDY [J].
BARNES, JC ;
HUME, DN .
INORGANIC CHEMISTRY, 1963, 2 (03) :444-&
[4]   Copper-catalyzed aerobic phosphonation of sp3 C-H bonds [J].
Basle, Olivier ;
Li, Chao-Jun .
CHEMICAL COMMUNICATIONS, 2009, (27) :4124-4126
[5]   Copper(II) bromide: A simple and selective monobromination reagent for ElectronRich aromatic compounds [J].
Bhatt, Suchitra ;
Nayak, Sandip K. .
SYNTHETIC COMMUNICATIONS, 2007, 37 (7-9) :1381-1388
[6]   C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines [J].
Brasche, Gordon ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) :1932-1934
[7]   CUPRIC HALIDE HALOGENATIONS [J].
CASTRO, CE ;
GAUGHAN, EJ ;
OWSLEY, DC .
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (02) :587-&
[8]   Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant [J].
Chen, Xiao ;
Hao, Xue-Shi ;
Goodhue, Charles E. ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6790-6791
[9]   Copper-catalyzed aerobic oxidative amidation of terminal alkynes: Efficient synthesis of ynamides [J].
Hamada, Tetsuya ;
Ye, Xuan ;
Stahl, Shannon S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (03) :833-+
[10]   Mechanistic study of asymmetric oxidative biaryl coupling: Evidence for self-processing of the copper catalyst to achieve control of oxidase vs oxygenase activity [J].
Hewgley, J. Brian ;
Stahl, Shannon S. ;
Kozlowski, Marisa C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (37) :12232-+
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