Synthesis of the multisubstituted halogenated olefins via cross-coupling of dihaloalkenes with alkylzinc bromides

被引:55
作者
Andrei, D [1 ]
Wnuk, SF [1 ]
机构
[1] Florida Int Univ, Dept Chem & Biochem, Miami, FL 33199 USA
关键词
D O I
10.1021/jo051980e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The 1-fluoro-1-haloalkenes undergo Pd-catalyzed Negishi cross-couplings with primary alkylzinc bromides to give multisubstituted fluoroalkenes. The alkylation was trans-selective giving pure Z-fluoroalkenes in most cases. The highest yields were obtained with Pd-2(dba)(3) and PdCl2(dppb) catalysts but the best stereochemical outcome was obtained with less reactive Pd(PPh3)(4). The tertiary alkylzincs also produced desired fluoroalkenes in high yields. Coupling of beta,beta-dichloro styrene with organozinc reagent resulted in the formation of monocoupled product.
引用
收藏
页码:405 / 408
页数:4
相关论文
共 35 条