Oxidative Rearrangement Coupling Reaction for the Functionalization of Tetrahydro-β-carbolines with Aromatic Amines

Novel methodology for efficient functionalization of tetrahydro-β-carbolines (THβCs) has been established via an unexpected oxidative rearrangement coupling reaction. Treatment of THβCs with photogenerated singlet oxygen (1O2) afforded unstable dioxetanes, followed by further transformation to construct new bond in the presence of TFA. This operationally simple protocol exhibits broadly functional group-tolerant and allows for last-stage functionalization of complex drug-like molecules.