Trans- and cis-selective Lewis acid catalyzed hydrogermylation of alkynes

被引：81

作者：

Schwier, T ^{[1
]}

Gevorgyan, V ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 23期

关键词：

D O I：

10.1021/ol0521026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first examples of Lewis acid catalyzed hydrogermylation of alkynes have been demonstrated. It was found that this method has much higher functional group compatibility compared to the known Lewis acid catalyzed hydrosilylation and hydrostannation reactions. Remarkably, the stereochemical outcome of this hydrogermylation reaction depends on the nature of the alkyne used: proceeding via a trans-addition pathway with simple alkynes and cis-addition with propiolates. Mechanistic studies strongly support the proposed rationale on the origins of cis-selectivity in the hydrogermylation of activated alkynes.

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页码：5191 / 5194

页数：4

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