Deaminative Strategy for the Visible-Light-Mediated Generation of Alkyl Radicals

Abstract

A deaminative strategy for the visible-light-mediated generation of alkyl radicals from redox-activated primary amine precursors is described. Abundant and inexpensive primary amine feedstocks, including amino acids, were converted in a single step into redox-active pyridinium salts and subsequently into alkyl radicals by reaction with an excited-state photocatalyst. The broad synthetic potential of this protocol was demonstrated by the alkylation of a number of heteroarenes under mild conditions.

Keywords: alkyl radicals; amino acids; deamination; photoredox catalysis; redox chemistry.