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

Ahmed Fnaiche, Bianca Bueno, Claire McMullin, Alexandre Gagnon

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3 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

Funding

This work was supported by the Natural Sciences and Engineering Research Council of Canada (NSERC) and by the Centre in Green Chemistry and Catalysis (CGCC). We thank Rémi Edouard and Suzanne Heurtaux for their assistance with this work. We thank Dr. Thierry Maris from the Plateforme de diffraction des rayons X du département de chimie de l'Université de Montréal for the X-ray structures and for useful discussions. We thank Dr. Alexandre Arnold for advanced NMR experiments and for useful discussions. This research made use of the Anatra High Throughput Computing (HTC) Cluster at the University of Bath. The authors gratefully acknowledge the University of Bath's Research Computing Group (doi.org/10.15125/b6cd-s854) for their support in this work. This work was supported by the Natural Sciences and Engineering Research Council of Canada (NSERC) and by the Centre in Green Chemistry and Catalysis (CGCC). We thank Rémi Edouard and Suzanne Heurtaux for their assistance with this work. We thank Dr. Thierry Maris from the Plateforme de diffraction des rayons X du département de chimie de l'Université de Montréal for the X‐ray structures and for useful discussions. We thank Dr. Alexandre Arnold for advanced NMR experiments and for useful discussions. This research made use of the Anatra High Throughput Computing (HTC) Cluster at the University of Bath. The authors gratefully acknowledge the University of Bath's Research Computing Group (doi.org/10.15125/b6cd‐s854) for their support in this work.

FundersFunder number
Natural Sciences and Engineering Research Council of Canada
University of Bath

    Keywords

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

    ASJC Scopus subject areas

    • General Chemistry

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