Catalytic Deprotonative α-Formylation of Heteroarenes by an Amide Base Generated in Situ from Tetramethylammonium Fluoride and Tris(trimethylsilyl)amine

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6 Citations (Scopus)

Abstract

Heteroarene formylations in DMF solution proceed in the presence of an amide base catalyst generated in situ from tetramethylammonium fluoride (TMAF) and tris(trimethylsilyl)amine (N(TMS)3). The reaction proceeds at room temperature and has an operationally simple procedure. Various heteroarenes, including benzothiophene, thiophene, benzothiazole, oxazole, and indole derivatives, can be formylated with high functional group tolerance.

Original languageEnglish
Pages (from-to)443-451
Number of pages9
JournalOrganic Process Research and Development
Volume23
Issue number4
DOIs
Publication statusPublished - 2019 Apr 19

Keywords

  • amide base catalyst
  • anions
  • formylation
  • heteroarenes
  • room-temperature deprotonation

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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