Palladium-catalyzed intramolecular tandem dearomatization of indoles for the synthesis of tetracyclic indolines

Abstract

A highly diastereoselective, atom-economical, and palladium-catalyzed Heck protocol for the assembly of structurally diverse indoline scaffolds with vicinal tertiary as well as quaternary stereocenters is described, starting from readily available N-halobenzoyl o-haloaniline derivatives and phenylboronic acids. This cascade annulation reaction, which is scalable and conducts under an ambient atmosphere, provides the valuable tetracyclic indoline derivatives in an efficient and straightforward way.

Keywords

• Tetracyclic indoline derivatives
• Palladium-catalyzed
• Aryl halides
• Phenylboronic acids
• Heck reaction