Gold-Catalyzed C-H Annulation of Anthranils with Alkynes: A Facile, Flexible, and Atom-Economical Synthesis of Unprotected 7-Acylindoles

Hongming Jin; Long Huang; Jin Xie; Matthias Rudolph; Frank Rominger; A Stephen K Hashmi

doi:10.1002/anie.201508309

Gold-Catalyzed C-H Annulation of Anthranils with Alkynes: A Facile, Flexible, and Atom-Economical Synthesis of Unprotected 7-Acylindoles

Angew Chem Int Ed Engl. 2016 Jan 11;55(2):794-7. doi: 10.1002/anie.201508309. Epub 2015 Nov 26.

Authors

Hongming Jin¹, Long Huang¹, Jin Xie¹, Matthias Rudolph¹, Frank Rominger¹, A Stephen K Hashmi^{2

3}

Affiliations

¹ Institut für Organische Chemie, Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg (Germany).
² Institut für Organische Chemie, Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg (Germany). hashmi@hashmi.de.
³ Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi Arabia. hashmi@hashmi.de.

PMID: 26610069
DOI: 10.1002/anie.201508309

Abstract

The gold-catalyzed C-H annulation of anthranil derivatives with alkynes offers a facile, flexible, and atom-economical one-step route to unprotected 7-acylindoles. An intermediate α-imino gold carbene, generated by an intermolecular reaction, promotes ortho-aryl C-H functionalization to afford the target products. The transformation proceeds with a broad range of substrates under mild conditions. Moreover, the obtained functionalized indole products represent a versatile platform for the construction of diverse indolyl frameworks.

Keywords: CH functionalization; alkynes; gold carbenoids; gold catalysis; indoles.

Publication types

Research Support, Non-U.S. Gov't