One-Pot Transformation of Aldehydes to Ketones via Minisci-Type Reaction of Imines

Org Lett. 2023 Dec 8;25(48):8751-8755. doi: 10.1021/acs.orglett.3c03764. Epub 2023 Nov 28.

Abstract

A method for the conversion of aldehydes to ketones via the preliminary formation of aldiminines is described. The imines are involved in acid promoted Minisci-type reaction with alkyl radicals generated from esters of N-hydroxylphthalimide under photoredox conditions. Aminyl radical cations formed after the addition of the iminium ions are believed to be key intermediates, which determine the reaction outcome.