Palladium-catalyzed synthesis of indoles by reductive N-heteroannulation of 2-nitrostyrenes

被引：117

作者：

Soderberg, BC

Shriver, JA

机构：

[1] Department of Chemistry, West Virginia University, Morgantown, WV 26506-6045

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 17期

关键词：

D O I：

10.1021/jo970516+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium-phosphine catalyzed reductive N-heteroannulation of 2-nitrostyrenes, in the presence of carbon monoxide, producing indoles has been developed. Indoles were obtained, in moderate to excellent yield, from substituted 2-nitrostyrenes having either electron-withdrawing (NO2 and CO2Me) or electron-donating (Br, OH, Me, OMe, and OTf) substituents on the aromatic ring. Best results were obtained using palladium diacetate (6 mol %) together with triphenylphosphine (24 mol %) as the catalytic system, under 4 atm of carbon monoxide in acetonitrile at 70 degrees C. Other palladium(II) and palladium(0) complexes also catalyze the reaction.

引用

页码：5838 / 5845

页数：8

共 72 条

[1] PALLADIUM COMPLEX-CATALYZED INTERMOLECULAR REDUCTIVE N-HETEROCYCLIZATION - NOVEL SYNTHESIS OF QUINAZOLINE DERIVATIVES FROM 2-NITROBENZALDEHYDE OR 2-NITROPHENYL KETONES WITH FORMAMIDE [J].