Issue 21, 2021

N-Heterocyclic carbene-catalyzed radical ring-opening acylation of oxime esters with aldehydes

Abstract

A cross-coupling of cycloketone oxime esters with aldehydes catalyzed by N-heterocyclic carbenes via a radical pathway was established. This modular protocol features easy operation, no external oxidants or reductants, and a broad functional group compatibility. The merit of this method was showcased by late-stage modification of complicated aldehydes derived from the medical intermediate pregnenolone and natural product diacetone-D-glucose.

Graphical abstract: N-Heterocyclic carbene-catalyzed radical ring-opening acylation of oxime esters with aldehydes

Supplementary files

Article information

Article type
Research Article
Submitted
09 jul 2021
Accepted
30 aug 2021
First published
01 sep 2021

Org. Chem. Front., 2021,8, 6074-6079

N-Heterocyclic carbene-catalyzed radical ring-opening acylation of oxime esters with aldehydes

Z. Zhang, X. Zou, Z. Li, Y. Gao, Y. Qu, Y. Quan, Y. Zhou, J. Li, J. Sun and K. Guo, Org. Chem. Front., 2021, 8, 6074 DOI: 10.1039/D1QO01015H

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