N-Bromosuccinimide (NBS)-Catalyzed C–H Bond Functionalization: An Annulation of Alkynes with Electron Withdrawing Group (EWG)-Substituted Acetyl Indoles for the Synthesis of Carbazoles

Abstract

An N-bromosuccinimide-catalyzed intermolecular annulation of acetyl indoles with alkynes was developed, allowing for regioselective formation of valuable carbazoles through direct C-H bond functionalization. The readily available catalyst, wide substrate scope, gram scale synthesis, and mild conditions make this method practical. Mechanistic investigations indicate that the bromination of acetyl indole takes place to generate a bromide intermediate, followed by coupling with an alkyne and intramolecular cycloaromatization to furnish carbazole products.