A versatile synthesis of substituted benzimidazolium salts by an amination/ring closure sequence

A versatile synthesis of substituted benzimidazolium salts by an amination/ring closure sequence
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DOI:
10.1021/ol016254m
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发表时间:
2001-08-23
期刊:
影响因子:
5.2
通讯作者:
Diver, ST
Diver, ST
中科院分区:
化学1区
文献类型:
--
作者:
Rivas, FM;Riaz, U;Diver, ST

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报道了一种基于连续的Buchwald-Hartwig胺化和闭环来生产苯并咪唑鎓盐的新方法。使用该方法可以制备多种不同的苯并咪唑鎓盐。带有α-手性基团的胺进行反应以提供手性苯并咪唑鎓盐。在杂环上缺少C2取代基的盐容易去质子化以得到亲核卡宾。
[GRAPHICS]A new method to produce benzimidazolium salts based on a successive Buchwald-Hartwig amination and ring closure is reported. A variety of different benzimidazolium salts can be prepared using this procedure. Amines that bear an alpha -chiral group undergo the reaction to furnish chiral benzimidazolium salts. The salts that lack a C2 substituent on the heterocycle are readily deprotonated to give nucleophilic carbenes.