Access to α-Hydroxy Amides via a Practical Metal-Free "One-Pot" Tandem Reaction Involving Aerobic C(sp³)-H Hydroxylation and C(sp²)-C(sp³) Cleavage

Xiao Zhang, Yang Yu, Wenjie Li, Lei Shi and Hao Li*

*School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China, Email: hli77ecust.edu.cn

X. Zhang, Y. Yu, W. Li, L. Shi, H. Li, J. Org. Chem., 2022, 87, 16263-16275.

DOI: 10.1021/acs.joc.2c01839

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Abstract

A flexible metal-free cascade reaction involving aerobic C(sp³)-H hydroxylation and decarbonylation introduces valuable secondary alcohol groups at the α-position of N-aryl amides with high regioselectivity and functional group tolerance.

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proposed mechanism

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Key Words

α-hydroxylation, decarbonylation, oxygen

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ID: J42-Y2022