PALLADIUM-CATALYZED COUPLING REACTIONS OF (ALPHA-ETHOXYVINYL)TRIMETHYLSTANNANE WITH VINYL AND ARYL TRIFLATES

被引：76

作者：

KWON, HB ^{[1
]}

MCKEE, BH ^{[1
]}

STILLE, JK ^{[1
]}

机构：

[1] COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80523

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 10期

关键词：

D O I：

10.1021/jo00297a029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium-catalyzed cross-coupling reaction of vinyl triflates and halides with (α-ethoxyvinyl)trimethylstannane gives high yields of 2-ethoxy 1,3-dienes, which can be hydrolyzed to the corresponding α,β-unsaturated ketones. Aryl triflates undergo an analogous coupling reaction, providing a facile method for replacing the hydroxyl group of a phenol by an acyl group. The use of (α-ethoxyvinyl)trimethylstannane in palladium-catalyzed carbonylative coupling gives rise to vinyl and aryl α-ethoxyvinyl ketones and indirectly to the corresponding a-diketones (which result from their hydrolysis) and glyoxylates (which result from their ozonolysis). © 1990, American Chemical Society. All rights reserved.

引用

页码：3114 / 3118

页数：5

共 36 条

[21] PALLADIUM-CATALYZED COUPLING OF 2-BROMOANILINES WITH VINYLSTANNANES - A REGIOCONTROLLED SYNTHESIS OF SUBSTITUTED INDOLES [J].