Deprotonative coupling of pyridines with aldehydes catalyzed by an HMDS-amide base generated in situ

Masanori Shigeno, Kunihito Nakaji, Akihisa Kajima, Kanako Nozawa-Kumada, Yoshinori Kondo

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

Herein, the deprotonative functionalization of pyridine derivatives with aldehydes under ambient conditions has been demonstrated using an amide base generated in situ from a catalytic amount of CsF and a stoichiometric amount of tris(trimethylsilyl)amine (N(TMS)3). Pyridine substrates bearing two electron-withdrawing substituents (i.e., fluoro, chloro, bromo, and trifluoromethyl moieties) at the 3- and 5-positions efficiently react at the 4-position with various aldehydes including arylaldehydes, pivalaldehyde, and cyclohexanecarboxaldehyde.

Original languageEnglish
Pages (from-to)1179-1182
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume67
Issue number11
DOIs
Publication statusPublished - 2019

Keywords

  • Amide base generated in situ
  • Deprotonative functionalization
  • Pyridine

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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