Chemistry of sulfonylmethyl isocyanides. 45. A direct synthesis of 2-(trimethylstannyl)pyrroles from Michael acceptors and stannylated tosylmethyl isocyanide

被引：43

作者：

Dijkstra, HP ^{[1
]}

ten Have, R ^{[1
]}

van Leusen, AM ^{[1
]}

机构：

[1] Univ Groningen, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 16期

关键词：

D O I：

10.1021/jo972216y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of 2-(trimethylstannyl)pyrroles 3, with substituents at the 3- and 4-positions, is synthesized efficiently by a base-induced reaction of stannylated TosMIC with Michael accepters. Stills cross-couplings with bromobenzene and double cross-couplings with 1,4-dibromobenzene have been achieved successfully with the N-methyl derivative (5a) and the N-Boc derivative (6a) of 3-benzoyl-2-(trimethylstannyl)-4-phenylpyrrole (3a), despite the bulk of these stannylpyrroles. Homo coupling reactions of the same stannylpyrroles with the corresponding bromopyrroles (prepared from stannylpyrroles 3 and NBS) were unsuccessful, probably for steric reasons.

引用

页码：5332 / 5338

页数：7

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