INDOL-2-YLTRIBUTYLSTANNANE - A VERSATILE REAGENT FOR 2-SUBSTITUTED INDOLES

被引：77

作者：

LABADIE, SS

TENG, E

机构：

[1] Syntex Discovery Research, Palo Alto

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 15期

关键词：

D O I：

10.1021/jo00094a042

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general method for 2-substituted indoles via the palladium-catalyzed coupling of indol-2-ylstannanes is described. (N-Methylindol-2-yl)tributylstannane (1) reacts with a variety of electrophiles under very mild conditions: [N-tert-Butoxycarbonyl)indol-2-yl]tributylstannane (3) is much less reactive in the coupling reactions and reacts only with certain activated electrophiles. [N-[[(Trimethylsilyl)ethoxy]methylindol-2-yl]tributylstannane (4) behaves similarly to 1 and the removal of the [(trimethylsilyl)ethoxy]methyl group can be achieved with tetra-n-butylammonium fluoride in DMF in the presence of ethylenediamine.

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页码：4250 / 4254

页数：5

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