Acyl-Directed ortho-Borylation of Anilines and C7 Borylation of Indoles using just BBr3

Saqib A. Iqbal, Jessica Cid, Richard J. Procter, Marina Uzelac, Kang Yuan, Michael J. Ingleson

Research output: Contribution to journalArticlepeer-review

72 Citations (SciVal)

Abstract

Indoles are privileged heterocycles found in many biologically active pharmaceuticals and natural products. However, the selective functionalization of the benzenoid moiety in indoles in preference to the more reactive pyrrolic unit is a significant challenge. Herein we report that N-acyl directing groups enable the C7-selective C−H borylation of indoles using just BBr3. This transformation shows some functional-group tolerance and notably proceeds with C6 substituted indoles. The directing group can be readily removed in situ and the products isolated as the pinacol boronate esters. Acyl-directed electrophilic borylation can be extended to carbazoles and anilines with excellent ortho selectivity. 4-amino-indoles are amenable to this process, with acyl group installation and directed electrophilic C−H borylation enabling selective formation of C5-BPin-indoles.

Original languageEnglish
Pages (from-to)15381-15385
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number43
DOIs
Publication statusPublished - 21 Oct 2019

Bibliographical note

Publisher Copyright:
© 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

Keywords

  • boranes
  • borenium
  • borylation
  • directing groups
  • electrophilic aromatic substitution

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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