Friedel-Crafts alkylation of indoles with trichloroacetimidates

Tamie Suzuki, John D Chisholm

Research output: Contribution to journalArticle

Abstract

Substituted indole scaffolds are often utilized in medicinal chemistry as they regularly possess significant pharmacological activity. Therefore the development of simple, inexpensive and efficient methods for alkylating the indole heterocycle continues to be an active research area. Reported are reactions of trichloroacetimidate electrophiles and indoles to address the challenges of accessing alkyl decorated indole structures. These alkylations perform best when either the indole or the imidate is functionalized with electron withdrawing groups to avoid polyalkylation.

Original languageEnglish (US)
Pages (from-to)1325-1329
Number of pages5
JournalTetrahedron Letters
Volume60
Issue number19
DOIs
StatePublished - May 9 2019

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Indoles
Alkylation
Imidoesters
Pharmaceutical Chemistry
Scaffolds
Pharmacology
Electrons
indole
trichloroacetamide
Research

Keywords

  • Alkylation
  • Friedel-Crafts
  • Indole
  • Lewis acid

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Friedel-Crafts alkylation of indoles with trichloroacetimidates. / Suzuki, Tamie; Chisholm, John D.

In: Tetrahedron Letters, Vol. 60, No. 19, 09.05.2019, p. 1325-1329.

Research output: Contribution to journalArticle

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