Nickel complexes catalyzed Heck reaction of iodobenzene and methyl acrylate

被引：51
作者：
Ma, SY
Wang, HJ
Gao, KM
Zhao, FY [1 ]
机构：
[1] Chinese Acad Sci, Changchun Inst Appl Chem, State Key Lab Electroanalyt Chem Lab, Changchun, Peoples R China
[2] Suihua Coll, Dept Chem, Suihua 152061, Peoples R China
[3] Changchun Univ Technol, Sch Chem Engn, Changchun 130012, Peoples R China
来源：
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2006年 / 248卷 / 1-2期
关键词：
Heck reaction; nickel complexes; solvent effects; ligand concentration;
D O I：
10.1016/j.molcata.2005.12.013
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：
Nickel appears the most promising for the replacement of palladium among the inexpensive transition metals for that it is active for Heck reaction and about 500 times cheaper than palladium. In this article, we describe our recent results in the area of nickel-catalyzed Heck vinylations. Main focus is on the influence of ligand concentration in different organic solvents and the effects of the addition of water. The conversion is high in NMP and increases with increasing of PPh3/Ni ratio; in ethanol and toluene the conversion presents a maximum value on Ni(PPh3)(2). The effect of the addition of water is sensitive to the concentration of PPh3 and the nature of solvent, it was well explained with the formation and transfer of the active species in the different solvent systems. (c) 2005 Elsevier B.V. All rights reserved.
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页码：17 / 20
页数：4
相关论文
共 14 条
[1]   Heck reaction using nickel/TPPTS catalyst and inorganic base on supported ethylene glycol phase [J].
Bhanage, BH ;
Zhao, FY ;
Shirai, M ;
Arai, M .
CATALYSIS LETTERS, 1998, 54 (04) :195-198
[2]   NICKEL-CATALYZED COUPLING OF ACTIVATED ALKENES WITH ORGANIC HALIDES [J].
BOLDRINI, GP ;
SAVOIA, D ;
TAGLIAVINI, E ;
TROMBINI, C ;
RONCHI, AU .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 301 (03) :C62-C64
[3]   RECENT DEVELOPMENTS AND NEW PERSPECTIVES IN THE HECK REACTION [J].
CABRI, W ;
CANDIANI, I .
ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (01) :2-7
[4]   FINE FEATHERS MAKE FINE BIRDS - THE HECK REACTION IN MODERN GARB [J].
DE MEIJERE, A ;
MEYER, FE .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1994, 33 (23-24) :2379-2411
[5]  
de Meijere A, 1994, ANGEW CHEM, V106, P2473, DOI DOI 10.1002/ANGE.19941062307
[6]  
GABRE D, 1992, ULLMANNS ENCY IND A, V7, P99
[7]   COORDINATION CHEMISTRY AND MECHANISMS OF METAL-CATALYZED CC-COUPLING REACTIONS .7. HECK VINYLATION OF ARYL HALIDES WITH N-BUTYL ACRYLATE - RELEVANCE OF PC BOND-CLEAVAGE TO CATALYST DEACTIVATION [J].
HERRMANN, WA ;
BROSSMER, C ;
OFELE, K ;
BELLER, M ;
FISCHER, H .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1995, 103 (03) :133-146
[8]   Ni(0) catalyzed reactions of aryl and vinyl halides with alkenes and alkynes [J].
Iyer, S ;
Ramesh, C ;
Ramani, A .
TETRAHEDRON LETTERS, 1997, 38 (49) :8533-8536
[9]   THE VINYLATION OF BROMOBIPHENYLS USING HOMOGENEOUS NICKEL-CATALYSTS [J].
KELKAR, AA ;
HANAOKA, T ;
KUBOTA, Y ;
SUGI, Y .
CATALYSIS LETTERS, 1994, 29 (1-2) :69-75
[10]   CONDENSATION OF ORGANIC BROMIDES WITH VINYL COMPOUNDS CATALYZED BY NICKEL-COMPLEXES IN THE PRESENCE OF ZINC [J].
LEBEDEV, SA ;
LOPATINA, VS ;
PETROV, ES ;
BELETSKAYA, IP .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 344 (02) :253-259
12