Light-activated hypervalent iodine agents enable diverse aliphatic C–H functionalization

Abstract

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 substantial interest in the development of general synthetic platforms that enable the efficient diversification of aliphatic C–H bonds. Here we report a hypervalent iodine reagent that releases a potent hydrogen atom abstractor for C–H activation under mild photochemical conditions. Using this reagent, we demonstrate 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 directly transform C–H bonds into diverse functionalities, including C–S, C–Cl, C–Br, C–I, C–O, C–N, C–C and C=C bonds. Aliphatic C–H functionalization is a valuable tool in organic synthesis. Now a hypervalent iodine reagent has been shown to release a potent hydrogen atom abstractor for C–H activation under mild photochemical conditions. This enables the transformation of C–H bonds into diverse functional groups with tunable control over the site selectivity.