Use of tetramethylammonium fluoride (TMAF) and alkali metal alkoxides as an activator for catalytic deprotonative functionalization of heteroaromatic C(sp2)-H bonds

Kiyofumi Inamoto, Hitomi Okawa, Shoko Kikkawa, Yoshinori Kondo

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

Abstract

Tetramethylammonium fluoride (TMAF) and some alkali metal alkoxides were found to be effective activators for deprotonative functionalization of heteroarenes. Onium amide bases, generated in situ from the combination of aminosilanes and a catalytic amount of TMAF or alkali metal alkoxides efficiently deprotonated C-H bonds of a series of heteroarenes in the presence of an electrophile such as ketones and aldehydes under mild conditions (room temperature). Addition products were obtained generally in good yields, thus providing a highly practical and efficient deprotonation method.

Original languageEnglish
Pages (from-to)7917-7922
Number of pages6
JournalTetrahedron
Volume70
Issue number43
DOIs
Publication statusPublished - 2014 Oct 28

Keywords

  • Alkali metal alkoxides
  • Deprotonation
  • Heteroarenes
  • Tetramethylammonium fluoride

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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