Photoinduced Carbamoylation of C(sp3)–H Bonds with Isocyanates

Alkylbenzenes coupled with isocyanates at the benzylic position upon irradiation with visible light in the presence of an iridium photoredox catalyst, a bromide anion, and a nickel catalyst, producing N-substituted α-aryl amides. An analogous carbamoylation reaction of aliphatic C–H bonds of alkanes took place when UV light and a diaryl ketone were used instead of visible light and the iridium complex. The present reaction offers a straightforward and atom-economical method for the synthesis of carboxamides starting from hydrocarbons with one-carbon extension. Alkylbenzenes coupled with isocyanates at the benzylic position upon irradiation with visible light in the presence of an iridium photoredox catalyst, a bromide anion, and a nickel catalyst, producing N-substituted α-aryl amides. An analogous carbamoylation reaction of aliphatic C–H bonds of alkanes took place when UV light and a diaryl ketone were used instead of visible light and the iridium complex.