Oxidative Cross-Coupling of α-Amino Ketones with Alcohols Enabled by I₂-Catalyzed C-H Hydroxylation.

ABSTRACT: An I₂-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 N,O-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.

SUBMITTER: Wang Y 

PROVIDER: S-EPMC10594655 | biostudies-literature | 2023 Oct

REPOSITORIES: biostudies-literature