Nickel catalyzed chain walking cross-ele ctrophile coupling of alkyl and aryl halides and olefin hydroarylation enabled by electrochemical reduction.

The first electrochemical approach for the nickel-catalyzed cross-electrophile coupling was developed. This method provides a novel route to afford 1,1-diarylalkane derivatives from simple and readily available alkyl and aryl halides in good yields and excellent regioselectivities under mild conditions. The procedure shows good tolerance for a broad variety of functional groups and both primary and secondary alkyl halides can be used. Furthermore, the reaction was successfully scaled up to the multigram scale proving the potential for the industrial application. Mechanistic investigations suggested the formation of a nickel hydride in the electroreductive chain walking arylation which led to the additional development of a new nickel catalyzed hydroarylation of styrenes providing a series of 1,1-diaryl alkanes in good yields under mild reaction conditions.