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

Citation:

Zhu J, Dai C, Ma M, Yue Y, Fan* X. Visible light-mediated cross-coupling of electrophiles: synthesis of α-amino amides from isocyanates and ketimines. Organic Chemistry FrontiersOrganic Chemistry Frontiers. 2021;8:1227-1232.

摘要:

A catalytic system to synthesize α-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 α-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.