Transition-metal-free and base promoted C–C bond formation via C–N bond cleavage of organoammonium salts

Abstract

A transition-metal-free and base promoted C–C bond forming reaction of benzyl C(sp³)–H bond with organoammonium salts via C–N bond cleavage has been reported. Benzyl ammonium salts as well as cinnamyl ammonium salt could couple readily with various benzyl C(sp³)–H species, producing the corresponding products in moderate to excellent yields with good functional group tolerance. Late stage chemical manipulation enabled the specific 1,2-diarylethane structure of products transformed into useful olefin compounds via dehydrogenation, which further demonstrated the utility of this reaction.