Benzocarbazole Synthesis via Visible-Light-Accelerated Rh(III)-Catalyzed C-H Annulation of Aromatic Amines with Bicyclic Alkenes

Abstract

A visible-light-accelerated Rh(III)-catalyzed C-H annulation of aromatic amines with bicyclic alkenes for the synthesis of benzocarbazole derivatives was developed. In this approach, with the cooperation of rhodium catalysis and visible-light irradiation, various aromatic amines reacted with oxabicyclic alkenes and azabicyclic alkenes smoothly at room temperature, delivering the corresponding bridged oxa or aza tetrahydro benzocarbazoles in good to excellent yields. Moreover, a series of benzo[b]carbazoles were synthesized conveniently through further aromatization in one pot. The potential of this method was demonstrated via directing-group removal, derivatization, a scale-up reaction, and fluorescence investigations.