A Single Phosphine Ligand Allows Palladium-Catalyzed Intermolecular C-O Bond Formation with Secondary and Primary Alcohols

被引:181
作者
Wu, Xiaoxing [1 ]
Fors, Brett P. [1 ]
Buchwald, Stephen L. [1 ]
机构
[1] MIT, Dept Chem, Cambridge, MA 02139 USA
基金
美国国家卫生研究院;
关键词
arenes; C-O cross-coupling; ligand design; palladium; synthetic methods; UNACTIVATED ARYL HALIDES; ALIPHATIC-ALCOHOLS; COUPLING REACTIONS; REDUCTIVE ELIMINATION; OXYGEN HETEROCYCLES; EFFICIENT CATALYST; DIARYL ETHERS; BUTYL ETHERS; CHLORIDES; CONVERSION;
D O I
10.1002/anie.201104361
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Forging a bond: An efficient, general palladium catalyst for C-O bond-forming reactions of secondary and primary alcohols with a range of aryl halides has been developed using the ligand 1. Heteroaryl halides, and for the first time, electron-rich aryl halides can be coupled with secondary alcohols. A diverse set of substrate combinations are possible with just a single ligand, thus obviating the need to survey multiple ligands. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:9943 / 9947
页数:5
相关论文
共 36 条
[1]   An improved cu-based catalyst system for the reactions of alcohols with aryl halides [J].
Altman, Ryan A. ;
Shafir, Alexandr ;
Choi, Alice ;
Lichtor, Phillip A. ;
Buchwald, Stephen L. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (01) :284-286
[2]   Novel electron-rich bulky phosphine ligands facilitate the palladium-catalyzed preparation of diaryl ethers [J].
Aranyos, A ;
Old, DW ;
Kiyomori, A ;
Wolfe, JP ;
Sadighi, JP ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (18) :4369-4378
[3]  
Buckingham J., 1994, DICT NATURAL PRODUCT
[4]  
Burgos C. H., 2006, ANGEW CHEM, V118, P4427
[5]   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
[6]   Pd-Catalyzed Cross-Coupling Reactions of Amides and Aryl Mesylates [J].
Dooleweerdt, Karin ;
Fors, Brett P. ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2010, 12 (10) :2350-2353
[7]   Using intelligent/random library screening to design focused libraries for the optimization of homogeneous catalysts: Ullmann ether formation [J].
Fagan, PJ ;
Hauptman, E ;
Shapiro, R ;
Casalnuovo, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (21) :5043-5051
[8]   A highly active catalyst for Pd-catalyzed amination reactions: Cross-coupling reactions using aryl mesylates and the highly selective monoarylation of primary amines using aryl chlorides [J].
Fors, Brett P. ;
Watson, Donald A. ;
Biscoe, Mark R. ;
Buchwald, Stephen L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (41) :13552-+
[9]   Pd-Catalyzed Conversion of Aryl Chlorides, Triflates, and Nonaflates to Nitroaromatics [J].
Fors, Brett P. ;
Buchwald, Stephen L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (36) :12898-+
[10]   A General and Efficient Catalyst for Palladium-Catalyzed C-O Coupling Reactions of Aryl Halides with Primary Alcohols [J].
Gowrisankar, Saravanan ;
Sergeev, Alexey G. ;
Anbarasan, Pazhamalai ;
Spannenberg, Anke ;
Neumann, Helfried ;
Beller, Matthias .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (33) :11592-11598