Photo- and dioxygen-enabled radical C(sp3)-N(sp2) cross-coupling between guanidines and perfluoroalkyl iodides

A photo- and dioxygen-enabled intermolecular radical Csp(3)-Nsp(2) cross-coupling between guanidines and perfluoroalkyl iodides has been developed. N-2-Perfluoroalkacylguanidines, which are of biological importance, were obtained under mild conditions via Nsp(2)-perfluoroalkylation and subsequent hydrolysis. The role of dioxygen in the reaction system was tentatively elucidated; it was supposed to act as an electron shuttle (redox mediator).