Photoredox-Catalyzed Synthesis of α-Amino Acid Amides by Imine Carbamoylation

An operationally simple protocol for the photocatalytic carbamoylation of imines is reported. Easily available, bench-stable 4-amido Hantzsch ester derivatives serve as precursors to carbamoyl radicals that undergo rapid addition to N-aryl imines. The reaction proceeds under blue light irradiation in the presence of the photocatalyst 3DPAFIPN and Bronsted/Lewis acid additives. Mechanistic studies indicated a photoredox mechanism that involves carbamoyl radicals.

Automated summary

The study presents a straightforward protocol for the photocatalytic carbamoylation of imines using easily accessible and stable 4-amido Hantzsch ester derivatives as precursors to carbamoyl radicals. The reaction occurs under blue light irradiation in the presence of the photocatalyst 3DPAFIPN and acid additives, with mechanistic studies suggesting a photoredox mechanism involving carbamoyl radicals.