On the Barton Copper-Catalyzed C3-Arylation of Indoles using Triarylbismuth bis(trifluoroacetate) Reagents

Ahmed Fnaiche, Bianca Bueno, Claire McMullin, Alexandre Gagnon

Research output: Contribution to journalArticlepeer-review

2 Citations (SciVal)

Abstract

We disclose herein our detailed investigation into the Barton copper-promoted C3-arylation of indoles using triarylbismuth bis(trifluoroacetates). The arylation of unsubstituted 1H-indole using Barton’s conditions gave a low yield of the C3-arylated indole, along with small amounts of the product of double C2/C3-arylation and traces of the product of C2 arylation. On the contrary, the arylation of indoles blocked at the C2 position is highly efficient, affording the desired products of C3-arylation in good to excellent yields. The reaction operates under simple conditions, shows good substrate scope, excellent functional group compatibility, and allows the transfer of electron-neutral or deficient aryl groups. Computational studies propose a mechanism involving a trifluoroacetate-assisted C–H activation step.
Original languageEnglish
Article number e202200465
Number of pages23
JournalChemPlusChem
Volume88
Issue number8
Early online date27 Feb 2023
DOIs
Publication statusPublished - 31 Aug 2023

Keywords

  • Arylation
  • Copper catalysis
  • C−H functionalization
  • Indoles
  • Organobismuth compounds

ASJC Scopus subject areas

  • General Chemistry

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