A complementary approach to conjugated N-acyliminium formation through photoredox-catalyzed intermolecular radical addition to allenamides and allencarbamates

Abstract

An intermolecular radical addition, using photoredox catalysis, to allenamides and allencarbamates is reported. This transformation synthesizes N-acyl-N’-aryl-N,N’-allylaminals, and proceeds by a conjugated N-acyliminium intermediate that previously has principally been generated by electrophilic activation methods. The radical adds to the central carbon of the allene giving a conjugated N-acyliminium that undergoes nucleophilic addition by arylamines and alcohols.

Keywords

• allenamide
• allene
• intermolecular
• n-acyliminium
• photoredox