Metal-, photocatalyst-, and light-free late-stage C-H alkylation of N-heteroarenes with organotrimethylsilanes using persulfate as a stoichiometric oxidant

Herein we report that under oxidative conditions, benzylsilanes and heteroatom substituted silanes undergo homolytic cleavage to form C(sp(3))-centered radicals that can participate in C-H alkylation reactions with N-heteroarenes. These reactions take place under mild conditions with persulfate as a stoichiometric oxidant and do not require a metal, a photocatalyst, light, or high temperature, making the reactions suitable for late-stage C-H alkylation of complex molecules. The utility of the method was demonstrated by the preparation or functionalization of several structurally complex drugs and natural products.