通过胍的C-H胺化/乙酰氧基化反应实现氧化剂可切换的2-氨基苯并咪唑的选择性合成。

Oxidant-switchable selective synthesis of 2-aminobenzimidazoles via C-H amination/acetoxylation of guanidines.

作者信息

Chi Yue, Zhang Wen-Xiong, Xi Zhenfeng

机构信息

Beijing National Laboratory for Molecular Sciences, and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University , Beijing 100871, China.

出版信息

Org Lett. 2014 Dec 19;16(24):6274-7. doi: 10.1021/ol502815p. Epub 2014 Dec 4.

DOI:10.1021/ol502815p

PMID:25474397

Abstract

The iodine(III) compound promoted C-H amination and tandem C-H amination/acetoxylation of guanidines are achieved for the first time to provide efficiently 2-aminobenzimidazoles and acetoxyl-substituted 2-aminobenzimidazoles, respectively. The amount and type of iodine(III) compounds control the selective syntheses of two types of 2-aminobenzimidazoles. This reaction shows good regioselectivity when unsymmetrical substrates are used.

摘要

首次实现了碘（III）化合物促进的胍的C-H胺化反应以及串联C-H胺化/乙酰氧基化反应，分别高效地得到了2-氨基苯并咪唑和乙酰氧基取代的2-氨基苯并咪唑。碘（III）化合物的用量和类型控制着两种类型2-氨基苯并咪唑的选择性合成。当使用不对称底物时，该反应表现出良好的区域选择性。