Visible light-driven dearomatization of tryptamine-derived isocyanides through aggregation-based charge transfer

Aggregation-based charge transfer has emerged as an attractive concept in organic chemistry. In this work, we have demonstrated the ability of tryptamine-derived isocyanides to form aggregates, which enable a single electron transfer step to generate carbon-based-radical intermediates. The developed protocol is operationally simple, robust and demonstrates a novel approach to generate constrained spirocyclic scaffolds. Mechanistic and computational studies have elucidated key aspects associated with radical generation and photophysical properties of tryptamine-derived isocyanides.