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Dearomatization-Rearomatization Strategy for Reductive Cross-Coupling of Indoles with Ketones in Water

Zemin Wang, Huiying Zeng*, Chao-Jun Li*

*Lanzhou University, 222 Tianshui Road, Lanzhou 730000, People’s Republic of China; McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, Canada, Email: zenghylzu.edu.cn, cj.limcgill.ca

Z. Wang, H. Zeng, C.-J. Li, Org. Lett., 2019, 21, 2302-2306.

DOI: 10.1021/acs.orglett.9b00591 (free Supporting Information)



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Abstract

Due to the poor nucleophilicity of the nitrogen atom of indoles and the competing alkylation reaction at the C-3 position, the use of more sterically hindered ketones with a lower electrophilicity as N-alkylation reagents has been a great challenge. A dearomatization-rearomatization strategy enables a reductive cross-coupling of indoles with ketones in water in good yield.

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proposed mechanism



Key Words

indoles, N-alkylation, formate


ID: J54-Y2019