Photoredox-mediated Minisci C–H alkylation of N-heteroarenes using boronic acids and hypervalent iodine

Abstract

A photoredox-mediated Minisci C-H alkylation reaction of <i>N</i>-heteroarenes with alkyl boronic acids is reported. A broad range of primary and secondary alkyl groups can be efficiently incorporated into various <i>N</i>-heteroarenes using [Ru(bpy)₃]Cl₂ as photocatalyst and acetoxybenziodoxole as oxidant under mild conditions. The reaction exhibits excellent substrate scope and functional group tolerance, and offers a broadly applicable method for late-stage functionalization of complex substrates. Mechanistic experiments and computational studies suggest that an intramolecularly stabilized <i>ortho</i>-iodobenzoyloxy radical intermediate might play a key role in this reaction system.