Arylgermylation of alkenes by a cooperative photoactivation and hydrogen atom transfer strategy

Abstract

We present an efficient photoredox/HAT dual-catalyzed arylgermylation of alkenes using readily available alkenes, germyl hydrides and (hetero)aryl nitriles under mild conditions and thus provide a variety of high-functionality germanium-containing molecules with quaternary carbons. Control experiments and DFT calculations confirmed that cooperative photoredox/HAT results in the generation of germyl radical/(hetero)aryl nitrile radical anions. The in situ formed radicals can undergo sequential addition reactions with alkenes, resulting in the selective 1,2-germylarylation of alkenes. This protocol exhibits mild reaction conditions, good functional tolerances and a broad substrate scope, complementing the observed transition metal-catalyzed coupling reactions.