Photoinduced carbamoylation of ethereal C-H bonds using pentafluorophenyl isocyanate

An intermolecular carbamoylation of ethers has been achieved via photoinduced functionalization of ethereal C-H bonds in the presence of benzophenone at ambient temperature. The carbamoyl group, a one-carbon unit with a high oxidation state, derived from pentafluorophenyl isocyanate (C6F5NCO) is chemoselectively introduced at the position geminal to the oxygen functionality in a single step. The present reaction system effectively activates the tertiary C-H bond at the sterically hindered site of fused bicyclic systems, and enables introduction of the carbamoyl group, which is then available for further synthetic elaborations.