Visible-Light-Mediated Amination of π-Nucleophiles with N-Aminopyridinium Salts

J Org Chem. 2019 Dec 20;84(24):15834-15844. doi: 10.1021/acs.joc.9b02073. Epub 2019 Oct 17.

Abstract

N-Aminopyridinium salts generate nitrogen-centered radicals by means of photoredox catalysis. Herein, we report that they can be trapped by enol equivalents to give α-amino carbonyl compounds in excellent yields. The broad synthetic utility of this method is demonstrated by functionalization of ketones, aldehydes, esters enol equivalents, vinyl ethers, and 1,3-diketones without the need for prior conversion to enol derivatives. The developed method is easily scalable, offers broad substrate scope, high chemoselectivity.