Dual photoredox nickel-catalyzed silylation of aryl/heteroaryl bromides using hydrosilanes

Abstract

Dual Ni and Ir catalysis enables the preparation of arylsilanes having a (TMS)₃Si substituent from the corresponding aryl bromides and (TMS)₃SiH at 30 °C using visible-light irradiation. This protocol avoids strong bases, high temperature and air and moisture sensitive silyl reagents, providing the expected arylsilanes in moderate to good yields. The reaction was shown to proceed through a silyl radical, likely generated by hydrogen atom abstraction from (TMS)₃SiH by a bromide radical.