<i>N</i>-Acylcarbazoles and <i>N</i>-Acylindoles: Electronically Activated Amides for N–C(O) Cross-Coupling by N_lp to Ar Conjugation Switch

Abstract

The development of new amide precursors for selective, catalytic activation of carbon–nitrogen bonds in amides is a fundamental objective of this emerging reactivity manifold. We report the palladium-catalyzed Suzuki–Miyaura cross-coupling of N-acylcarbazoles and N-acylindoles with arylboronic acids by a highly selective N–C(O) cleavage. The key amide bond ground-state destabilization stems from Nlp to Ar conjugation and enables us for the first time to achieve reactivity similar to that for N-acylsulfonamide and N-acylcarbamate activation in simple anilides.

Topics & Concepts