NIS-mediated, light-promoted intramolecular C–N cascade enables rapid access to benzo[4,5]indolo[3,2-c]isoquinolines and their photocatalytic applications

Abstract

A metal- and base-free, N-iodosuccinimide-mediated, light-promoted intramolecular cascade reaction has been developed for the rapid construction of benzo[4,5]indolo[3,2-c]isoquinolines. This transformation proceeds through two sequential intramolecular C–N bond-forming events under mild conditions, affording densely fused nitrogen-rich polycycles with broad substrate scope and good functional-group tolerance. The resulting π-extended scaffolds exhibit intrinsic photophysical properties and function as organic photocatalysts for redox-neutral difunctionalization of acrylamides.