PEG-400 promoted Pd(OAc)2/DABCO-catalyzed cross-coupling reactions in aqueous media

被引:123
作者
Li, JH [1 ]
Hu, XC [1 ]
Liang, Y [1 ]
Xie, YX [1 ]
机构
[1] Human Normal Univ, Coll Chem & Chem Engn, Changsha 410081, Peoples R China
基金
中国国家自然科学基金;
关键词
PEG-400; Pd(OAc)(2)/DABCO; cross-coupling reaction; aryl halide; arylboronic acids; organotin compounds;
D O I
10.1016/j.tet.2005.09.138
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
PEG-400 [poly(ethylene glycol-400)] was found to improve the Pd(OAc)(2)/DABCO-catalyzed aqueous Suzuki-Miyaura and Stille cross-coupling reactions. In the presence of Pd(OAc)2, DABCO, and PEG-400, a variety of aryl halides were coupled with arylboronic acids or organotin compounds efficiently to afford the corresponding cross-coupled products in moderate to excellent yields. The turnover numbers was up to 900,000 for the Suzuki-Miyaura reaction and up to 9800 for the Stille reaction. The catalyst system was also effective for Heck and Sonogashira cross-coupling reactions to some extent. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:31 / 38
页数:8
相关论文
共 81 条
[1]   Highly active oxime-derived palladacycle complexes for Suzuki-Miyaura and Ullmann-type coupling reactions [J].
Alonso, DA ;
Nájera, C ;
Pacheco, MC .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16) :5588-5594
[2]   Sterically demanding, bioxazoline-derived N-heterocyclic carbene ligands with restricted flexibility for catalysis [J].
Altenhoff, G ;
Goddard, R ;
Lehmann, CW ;
Glorius, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15195-15201
[3]   An N-heterocyclic carbene ligand with flexible steric bulk allows Suzuki cross-coupling of sterically hindered aryl chlorides at room temperature [J].
Altenhoff, G ;
Goddard, R ;
Lehmann, CW ;
Glorius, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (31) :3690-3693
[4]   Efficient catalyst for the Suzuki-Miyaura coupling of potassium aryl trifluoroborates with aryl chlorides [J].
Barder, TE ;
Buchwald, SL .
ORGANIC LETTERS, 2004, 6 (16) :2649-2652
[5]   Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].
Barder, TE ;
Walker, SD ;
Martinelli, JR ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696
[6]   The Suzuki coupling of aryl chlorides in TBAB-water mixtures [J].
Bedford, RB ;
Blake, ME ;
Butts, CP ;
Holder, D .
CHEMICAL COMMUNICATIONS, 2003, (04) :466-467
[7]  
Bedford RB, 2002, ANGEW CHEM INT EDIT, V41, P4120, DOI 10.1002/1521-3773(20021104)41:21<4120::AID-ANIE4120>3.0.CO
[8]  
2-7
[9]   Palladium catalysts for the Suzuki cross-coupling reaction: An overview of recent advances [J].
Bellina, F ;
Carpita, A ;
Rossi, R .
SYNTHESIS-STUTTGART, 2004, (15) :2419-2440
[10]  
BOOTH RS, 2004, ORG LETT, V6, P225