Synthetic Access to gem-Difluoropropargyl Vinyl Ethers and Their Application to Propargyl Claisen Rearrangement

Toshitaka Okamura, Kenta Koyamada, Junichiro Kanazawa, Kazunori Miyamoto, Yoshiharu Iwabuchi, Masanobu Uchiyama, Naoki Kanoh

Research output: Contribution to journalArticlepeer-review

Abstract

With the increasing importance of fluorine to medicinal chemistry and other areas, methods to access various fluorinated compounds are needed. Herein, we report the synthesis of difluoropropargyl vinyl ethers from ketones and aldehydes using difluoropropargyl bromide dicobalt complexes. We applied difluoropropargyl vinyl ethers to the synthesis of difluorodienone or difluoroallene under thermal conditions and trifluoro-pyran under acid-catalyzed conditions.

Original languageEnglish
Pages (from-to)1911-1924
Number of pages14
JournalJournal of Organic Chemistry
Volume86
Issue number2
DOIs
Publication statusPublished - 2021 Jan 15
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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