Photoredox catalysed reductive aminomethylation of quaternary benzophenanthridine alkaloids

Nat Prod Res. 2023 Oct-Nov;37(21):3551-3555. doi: 10.1080/14786419.2022.2092732. Epub 2022 Jun 29.

Abstract

Reduction of C = N double bond is the most important phase I metabolism process of quaternary benzophenanthridine alkaloids (QBAs). Inspired by the NADPH mediated reduction in QBAs, a visible-light promoted reductive aminomethylation of QBAs for synthesis of 6-substituted benzophenanthridines was reported using QBAs and N,N-dimethylaniline as coupling partners in this study. An α-amino radical that derived from QBAs was supposed to be the key intermediate in this visible-light promoted reductive aminomethylation reaction.

Keywords: Dihydrobenzophenanthridine; photoredox catalysis; radical-radical coupling; reductive aminomethylation; visible light.