Selective C(sp³)−H Functionalization of Alkyl Esters with N-/S-/O-Nucleophiles Using Perfluoroalkyl Iodide as Oxidant

An efficient transition metal-free approach to achieve the selective cleavage of the α-carbonyl C(sp³)−H bond in alkyl esters by using inexpensive, low-toxic, and insensitive perfluoroalkyl iodide as the radical initiator has been developed. A variety of enamides, N-heterocycles, amides, thiophenols, and phenols could be successfully incorporated into functionalized alkyl groups by intermolecular amination, thioetherification, and etherification. The distinguishing features of this CDC reaction are its broad substrate scope, synthetic simplicity, and mild reaction conditions. (Figure presented.).