Iodine/Copper Iodide-Mediated C-H Functionalization: Synthesis of Imidazo[1,2-a]pyridines and Indoles from N-Aryl Enamines

Jing Liu, Wei Wei, Ting Zhao, Xuanyu Liu, Jie Wu, Wenquan Yu* and Junbiao Chang*

*College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou, Henan Province 450001, China, Email: wenquan_yuzzu.edu.cn, changjunbiaozzu.edu.cn

J. Liu, W. Wei, T. Zhao, X. Liu, J. Wu, W. Yu, J. Chang, J. Org. Chem., 2016, 81, 9326-9336.

DOI: 10.1021/acs.joc.6b01960

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Abstract

A practical intramolecular C-H functionalization reaction of N-aryl enamines with molecular iodine as the sole oxidant in the presence of copper iodide (CuI) provides diverse imidazo[1,2-a]pyridine and indole derivatives via I₂-mediated oxidative C-N and C-C bond formation, respectively. This reaction also works well with crude enamines.

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Key Words

imidazo[1,2-a]pyridines

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ID: J42-Y2016