PREPARATION OF BETA, BETA-DIFLUORO-ALPHA-(TRIFLUOROMETHYL)STYRENES BY PALLADIUM-CATALYZED COUPLING OF ARYL IODIDES WITH PENTAFLUOROPROPEN-2-YLZINC REAGENT

被引：47

作者：

MORKEN, PA ^{[1
]}

BURTON, DJ ^{[1
]}

机构：

[1] UNIV IOWA,DEPT CHEM,IOWA CITY,IA 52242

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 05期

关键词：

D O I：

10.1021/jo00057a032

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Substituted aromatic iodides are functionalized by pentafluoropropen-2-ylzinc, CF3C(ZnX)=CF2 (X = Br, I, or CF2=CCF3-), in the presence of Pd(PPh3)4 to give the corresponding arenes in good yields. This is particularly attractive for preparation of title styrenes substituted with groups such as -NO2 or CO2R, which are incompatible with organomagnesium reagents. The best yields of the title styrenes with electron-donating substituents were obtained in DMF. For electron-withdrawing substituents, the best results were achieved in triglyme. A correlation was observed between Hammett sigma constants and F-19 NMR chemical shifts (R = 0.93-0.99, n = 8) and 2J(F-F) coupling constants (R = 0.94, n = 8).

引用

页码：1167 / 1172

页数：6

共 38 条

[1] ROLE AND EFFECTS OF HALIDE-IONS ON THE RATES AND MECHANISMS OF OXIDATIVE ADDITION OF IODOBENZENE TO LOW-LIGATED ZEROVALENT PALLADIUM COMPLEXES PD0(PPH3)2 [J].