Visible light-mediated cross-coupling of electrophiles: synthesis of α-amino amides from isocyanates and ketimines

A catalytic system to synthesize alpha-amino amides from isocyanates and ketimines has been developed using visible light iridium photoredox catalysis via umpolung reactivity of ketimines. Cross-couplings between diverse ketimine and isocyanate substrates have been evaluated, affording the desired alpha-amino amide products in good yields. In addition, a metal-free catalytic system using perylene and N,N-diisopropylethylamine has been developed. Finally, single-step synthesis of the psychoactive drug benzodiazepine-2-one analogue from one of the coupling products has been achieved, indicating the great application potential of the synthetic method developed herein.

Automated summary

A catalytic system utilizing visible light iridium photoredox catalysis has been developed for synthesizing alpha-amino amides through the umpolung reactivity of ketimines. Cross-couplings between various ketimine and isocyanate substrates have been evaluated, leading to good yields of the desired products. Additionally, a metal-free catalytic system and the successful synthesis of a benzodiazepine-2-one analogue indicate the significant application potential of the developed synthetic method.