Photocatalytic three-component 1,2-boroarylation and carbopyridylation of alkene†

Abstract

In the present work, we developed a photocatalytic three-component 1,2-boroarylation of alkenes using readily available alkenes, bis(pinacolato)diboron, and (hetero)aryl nitriles in the presence of base and photocatalyst—to afford a diverse array of boryl-enriched 1,1-diarylalkane compounds. Alkylboronic pinacol esters were also found to be suitable substrates for the reaction, giving the corresponding carbopyridylation products. Control experiments and DFT calculations supported our proposed photoinduced generation of a boryl unit and aryl nitrile radical anion, which sequentially coupled to alkene. This protocol exhibited mild reaction conditions, good functional group tolerance and a one-pot procedure, serving as a complementary approach to transition-metal-catalyzed coupling reaction.