A Light-Activated Hypervalent Iodine Agent Enables Diverse Aliphatic C–H Functionalization

The functionalization of aliphatic C–H bonds is a crucial step in the synthesis and transformation of complex molecules relevant to medicinal, agricultural, and materials chemistry. As such, there is significant interest in the development of general synthetic platforms that will enable efficient diversification of aliphatic C–H bonds. Here, we report a new hypervalent iodine reagent that releases a potent hydrogen atom abstractor for C–H activation under mild photochemical conditions. Using this reagent, we demonstrate the selective (N-phenyltetrazole)thiolation of aliphatic C–H bonds for a broad scope of substrates. The synthetic utility of the thiolated products is showcased through various derivatizations. Simply by altering the radical trapping agent, our method can be used to directly transform C–H bonds into diverse functionalities, including C–S, C–Cl, C–Br, C–I, C–O, C–N, and C–C bonds.