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

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. (c) 2021 The Author(s). Published by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

Automated summary

A highly diastereoselective and atom-economical Heck protocol is described for the assembly of structurally diverse indoline scaffolds with vicinal tertiary and quaternary stereocenters, starting from readily available precursors. This cascade annulation reaction provides valuable tetracyclic indoline derivatives efficiently and straightforwardly.