Unlocking the reactivity of the C-In bond: alkyl indium reagents as a source of radicals under photocatalytic conditions.

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 a novel indium(i) bromide/lithium bromide system. Both steps, the formation of organoindiums and their cross-coupling are insensitive towards air and moisture and tolerate a wide variety of functional groups.