Unlocking the Reactivity of the C-In Bond: Alkyl Indium Reagents as a Source of Radicals Under Photocatalytic Conditions

Abstract

Generation of organic radicals from organometallic compounds is a key step in metallaphotoredox cross-coupling reactions. The ability of organoindium compounds to serve as sources of alkyl radicals under light promoted oxidative conditions is described. Organoindium reagents were used in dual photocatalytic/nickel cross-coupling with aryl bromides. These reagents can be conveniently obtained from primary, secondary and tertiary alkyl bromides and chlorides using novel indium(I) bromide/lithium bromide system. Both steps, the formation of organoindiums and their cross-coupling are insensitive towards air, moisture and tolerate wide variety of functional groups.