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

Org Lett

Institute of Catalysis for Energy and Environment, College of Chemistry and Chemical Engineering, Shenyang Normal University, Shenyang 110034, People's Republic of China.

Published: October 2021

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[]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.

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http://dx.doi.org/10.1021/acs.orglett.1c02709DOI Listing

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