Selectivity Control in Gold-Catalyzed Hydroarylation of Alkynes with Indoles: Application to Unsymmetrical Bis(indolyl)methanes

Euan B. McLean, Francesca M. Cutolo, Orla J. Cassidy, David J. Burns, Ai-Lan Lee

Research output: Contribution to journalArticle

Abstract

Gold-catalyzed hydroarylation of unactivated alkynes with indoles have previously been reported to proceed with double indole addition to produce symmetrical bis(indolyl)methanes (BIMs). We demonstrate for the first time that the selectivity of the gold-catalyzed reaction can be fully switched to allow for isolation of the vinylindole products instead. Furthermore, this selective reaction can be utilized to synthesize the more difficult to access unsymmetrical BIMs from readily available starting materials.

Original languageEnglish
Pages (from-to)6977-6981
Number of pages5
JournalOrganic letters
Volume22
Issue number17
Early online date26 Aug 2020
DOIs
Publication statusPublished - 4 Sep 2020

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Selectivity Control in Gold-Catalyzed Hydroarylation of Alkynes with Indoles: Application to Unsymmetrical Bis(indolyl)methanes'. Together they form a unique fingerprint.

  • Cite this