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KI-Catalyzed Oxidative Cyclization of Enamines and tBuONO to Access Functional Imidazole-4-Carboxylic Derivatives

Yingchun Li, Jixia Qiu, Peng Gao*, Le Zhai, Zi-Jing Bai and Huai-Juan Chen

*Shaanxi Key Laboratory of Phytochemistry, College of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji 721013, Shaanxi, P. R. China, Email:

Y. Li, J. Qiu, P. Gao, L. Zhai, Z.-J. Bai, H.-J. Chen, J. Org. Chem., 2022, 87, 15380-15388.

DOI: 10.1021/acs.joc.2c01943

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KI mediates a noble-metal-free oxidative cyclization of enamines with tBuONO as an aminating reagent and oxidant. This formal [4 + 1] cycloamination reaction provides imidazole-4-carboxylic derivatives with wide substrate scope and good functional tolerance.

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proposed mechanisms

Key Words

imidazoles, tBuONO

ID: J42-Y2022