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CuI-Catalyzed Aerobic Oxidative α-Aminaton Cyclization of Ketones to Access Aryl or Alkenyl-Substituted Imidazoheterocycles

Yuanfei Zhang, Zhengkai Chen, Wenliang Wu, Yuhong Zhang* and Weiping Su*

*Fujian Institute of Research on the Structure of Matter, Fuzhou, Fujian 350002; Department of Chemistry, Zhejiang University, Hangzhou 310027, China, Email: yhzhangzju.edu.cn, wpsufjirsm.ac.cn

Y. Zhang, Z. Chen, W. Wu, Y. Zhang, W. Su, J. Org. Chem., 2013, 78, 12494-12504.

DOI: 10.1021/jo402134x (free Supporting Information)


Abstract

A CuI-catalyzed aerobic oxidative synthesis of imidazo[1,2-a]pyridines from 2-aminopyridines and acetophenones is compatible with a broad range of functional groups. The reaction also enables the formation of alkenyl-substituted imidazoheterocycles by using unsaturated ketones as substrates. Preliminary mechanistic studies indicate that this reaction proceeds through a catalytic Ortoleva-King reaction.

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Key Words

imidazo[1,2-a]pyridines, oxygen


ID: J42-Y2013