Highly Chemoselective gem-Difluoropropargylation of Aliphatic Alcohols

Toshitaka Okamura, Syusuke Egoshi, Kosuke Dodo, Mikiko Sodeoka, Yoshiharu Iwabuchi, Naoki Kanoh

Research output: Contribution to journalArticle

Abstract

Despite the potential of α-fluoroethers in medicinal chemistry, their synthetic methods, especially etherification of aliphatic alcohols, have been limited. Herein, we developed two- and three-step gem-difluoropropargylation of aliphatic alcohols including amino acid derivatives and naturally occurring bioactive molecules. Highly chemoselective etherification proceeded by using the gem-difluoropropargyl bromide dicobalt complex in the presence of silver triflate and triethylamine. Decomplexation of dicobalt complexes was achieved by using cerium ammonium nitrate or N,N,N′-trimethylethylenediamine. The thus obtained gem-difluoropropargyl ethers were converted to various α-difluoroethers which are expected to be useful for medicinal chemistry.

Original languageEnglish
Pages (from-to)16002-16006
Number of pages5
JournalChemistry - A European Journal
Volume25
Issue number70
DOIs
Publication statusPublished - 2019 Dec 13

Keywords

  • chemoselectivity
  • dicobalt complex
  • difluoropropargylation
  • drug development

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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