Photoredox-Catalyzed C(sp3)–H Difluoroallylation of Amides

Abstract A photoredox-catalyzed, bromine-radical-mediated C(sp3)–H difluoroallylation of amides is disclosed. This modular approach exploits the hydrogen atom transfer (HAT) ability of photooxidatively generated bromine radicals to convert both cyclic and acyclic amides into the corresponding α-amino alkyl radicals that then are coupled with readily available trifluoromethyl alkenes. This method is distinguished by its mild conditions, broad substrate scope (30 examples), and the use of a simple HAT reagent, namely sodium bromide (NaBr). This strategy offers a promising paradigm for the incorporation of carbonyl isosteres into saturated aliphatic amines.