Visible light catalyzed arylsilylation of alkenes to construct silicon-containing 1,1-diaryl moieties

Abstract

We established an efficient photocatalyzed arylsilylation of alkenes, utilizing readily accessible silylboronates and (hetero)aryl nitriles in the presence of a base. This reaction proceeds through a photoredox-triggered cascade of single-electron transfers of base/silylboronate adducts and (hetero)aryl nitriles with the photocatalyst, leading to the formation of the silyl radicals and (hetero)aryl nitrile radical anions. This is followed by sequential coupling with alkenes, yielding valuable 1,1-diaryl derivatives with a silicon group at the β-position. This protocol features good functional group tolerance, mild reaction conditions, and broad substrate scopes, and thus can be applicable to the structural modification of bioactive molecules.