Hypervalent Iodine Reagents Enable C(sp²)-H Amidation of (Hetero)arenes with Iminophenylacetic Acids

Yue Pan, Zhengyi Liu, Peng Zou, Yali Chen and Yiyun Chen*

*Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 China, Email: yiyunchensioc.ac.cn

Y. Pan, Z. Liu, P. Zou, Y. Chen, Y. Chen, Org. Lett., 2022, 24, 6681-6685.

DOI: 10.1021/acs.orglett.2c02751

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Abstract

Sulfonamidyl (hetero)arenes can be synthesized by a C(sp²)-H amidation with bench-stable amidyl-iminophenylacetic acids in the presence of a hypervalent iodine reagent. The hypervalent iodine reagent covalently activates the iminophenylacetic acid for the facile sulfonamidyl radical generation under mild photocatalytic oxidative conditions.

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proposed mechanism

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Key Words

indoles, photochemistry, hypervalent iodine reagents

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ID: J54-Y2022