Oxidative Cross-Coupling of α-Amino Ketones with Alcohols Enabled by I-Catalyzed C-H Hydroxylation

Overview

Journal J Org Chem

Publisher American Chemical Society

Specialty Chemistry

Date 2023 Oct 9

PMID 37807762

Authors

Yingwei Wang

Mingrong Yang

Chichou Lao

Hanxuan Wang

Zhihong Jiang

Affiliations

Soon will be listed here.

Abstract

An I-catalyzed oxidative cross-coupling of α-amino ketones with a wide range of alcohols is described. Using a combination of air and dimethyl sulfoxide (DMSO) as oxidants, the protocol allows an efficient synthesis of α-carbonyl -acetals with high functional group tolerance and enables the late-stage introduction of α-amino ketones into biorelevant alcohols. Moreover, the present method can be used in the coupling of α-amino ketones with other kinds of nucleophiles, which demonstrates great generality for the functionalization of α-amino ketones. A preliminary mechanistic investigation suggests that C-H hydroxylation of α-amino ketones has been recognized as the key step followed by subsequent dehydration coupling.

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