Biphenyl-based phosphine: A well-defined, air-stable, and efficient ligand for the Mizoroki-Heck reaction

被引:39
作者
Nadri, Shirin [1 ]
Joshaghani, Mohammad [1 ,2 ]
Rafiee, Ezzat [1 ,2 ]
机构
[1] Razi Univ, Fac Chem, Kermanshah 67149, Iran
[2] Kermanshah Oil Refining Co, Kermanshah, Iran
关键词
C-C coupling; Mizoroki-Heck Reaction; Biphenyl-based phosphine; Palladium catalyst; CROSS-COUPLING REACTIONS; HIGHLY-ACTIVE CATALYST; ARYL CHLORIDES; BOND FORMATION; PALLADIUM CATALYSIS; C-C; HALIDES; ARYLATION; BROMIDES; OLEFINS;
D O I
10.1016/j.apcata.2009.04.038
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
An efficient and stereoselective catalytic system has been reported for the Mizoroki-Heck cross coupling using a moderately bulky and electron-rich biphenyl-based phosphine, P(o-C6H4C6H4Me)Ph-2 and a low Pd(OAc)(2) loading. It is found that the nature of olefin has more beneficial effect on the reaction times and yields than the aryl halide which may be due to more contribution of the coordination and/or insertion of the olefin in the rate-determining step of the Heck reaction. (C) 2009 Elsevier B.V. All rights reserved.
引用
收藏
页码:163 / 168
页数:6
相关论文
共 53 条
[1]   Anionic Pd(0) and Pd(II) intermediates in palladium-catalyzed Heck and cross-coupling reactions [J].
Amatore, C ;
Jutand, A .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (05) :314-321
[2]   Synthesis of medium ring heterocycles using an intramolecular Heck reaction [J].
Arnold, LA ;
Luo, WC ;
Guy, RK .
ORGANIC LETTERS, 2004, 6 (17) :3005-3007
[3]   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
[4]   Palladacyclic catalysts in C-C and C-heteroatom bond-forming reactions [J].
Bedford, RB .
CHEMICAL COMMUNICATIONS, 2003, (15) :1787-1796
[5]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[6]  
Beller M, 1998, EUR J INORG CHEM, P29
[7]   A highly active catalyst for Suzuki-Miyaura cross-coupling reactions of heteroaryl compounds [J].
Billingsley, Kelvin L. ;
Anderson, Kevin W. ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (21) :3484-3488
[8]  
Böhm VPW, 2001, CHEM-EUR J, V7, P4191
[9]   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
[10]   Kinetics and mechanistic aspects of the Heck reaction promoted by a CN-palladacycle [J].
Consorti, CS ;
Flores, FR ;
Dupont, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (34) :12054-12065