Visible-Light-Mediated Nucleophilic Addition of an α-Aminoalkyl Radical to Isocyanate or Isothiocyanate

A visible-light photoredox synthesis of alpha-amino amide or alpha-amino thioamide from N,N-dimethylaniline derivatives and aryl isocyanate or aryl isothiocyanate was developed. Bis[2-(4,6-difluorophenyl)pyridinato-C-2,N](picolinato)iridium(III) (Flrpic) was found to be the effective catalyst among six catalysts screened. The reaction involves generation of alpha-aminoalkyl radicals from tertiary amines, followed by radical addition to the electron-deficient carbon of isocyanate and isothiocyanate.