Direct synthesis of cinnamaldehyde derivatives by reaction of aryl bromides with 3,3-diacetoxypropene catalyzed by a palladium-tetraphosphine complex

被引:18
作者
Berthiol, F
Doucet, H
Santelli, M
机构
[1] Fac Sci & Tech St Jerome, Synth Organ Lab, CNRS, UMR 6180, F-13397 Marseille, France
[2] Univ Aix Marseille 3, F-13397 Marseille, France
关键词
palladium; tetraphosphine; catalysis; Heck reaction; aryl bromide;
D O I
10.1007/s10562-005-5869-z
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
The tetraphosphine all-cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane in combination with [Pd(C3H5)Cl](2) affords an efficient catalyst for the synthesis of cinnamaldehyde derivatives by reaction of aryl bromides with 3,3-diacetoxypropene. The reaction gave directly the cinnamaldehyde derivatives very selectively. The coupling reaction of heteroaryl bromides or sterically congested aryl bromides such as 2,4,6-trimethylbromobenzene also proceeds.
引用
收藏
页码:281 / 284
页数:4
相关论文
共 37 条
[1]   Orthopalladated triarylphosphite complexes as highly efficient catalysts in the Heck reaction [J].
Albisson, DA ;
Bedford, RB ;
Scully, PN .
TETRAHEDRON LETTERS, 1998, 39 (52) :9793-9796
[2]   An efficient palladium-catalyzed synthesis of cinnamaldehydes from acrolein diethyl acetal and aryl iodides and bromides [J].
Battistuzzi, G ;
Cacchi, S ;
Fabrizi, G .
ORGANIC LETTERS, 2003, 5 (05) :777-780
[3]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[4]   Tridentate SCS palladium(II) complexes: New, highly stable, recyclable catalysts for the heck reaction [J].
Bergbreiter, DE ;
Osburn, PL ;
Liu, YS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (41) :9531-9538
[5]   Heck reactions of aryl bromides with alk-1-en-3-ol derivatives catalysed by a tetraphosphine/palladium complex [J].
Berthiol, F ;
Doucet, H ;
Santelli, M .
TETRAHEDRON LETTERS, 2004, 45 (29) :5633-5636
[6]  
Berthiol F, 2003, SYNLETT, P841
[7]   Heck reaction of aryl halides with linear or cyclic alkenes catalysed by a tetraphosphine/palladium catalyst [J].
Berthiol, F ;
Doucet, H ;
Santelli, M .
TETRAHEDRON LETTERS, 2003, 44 (06) :1221-1225
[8]   Heck reaction with heteroaryl halides in the presence of a palladium-tetraphosphine catalyst [J].
Berthiol, F ;
Feuerstein, M ;
Doucet, H ;
Santelli, M .
TETRAHEDRON LETTERS, 2002, 43 (32) :5625-5628
[9]   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
[10]   High-turnover palladium catalysts in cross-coupling and Heck chemistry: A critical overview [J].
Farina, V .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (13-15) :1553-1582