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

  • Photo du rédacteur: Groupe Gagnon
    Groupe Gagnon
  • 2 mars 2023
  • 1 min de lecture

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.


 
 
 

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Alexandre Gagnon, Ph.D.

Professeur titulaire

Université du Québec à Montréal, Département de chimie

2101 Rue Jeanne-Mance, Montréal, Québec, Canada, H2X 2J6

Email: gagnon.alexandre@uqam.ca

Tel: 514.987.3000 ext 6856

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