A Copper-Catalyzed Reductive Defluorination of β-Trifluoromethylated Enones via Oxidative Homocoupling of Grignard Reagents

Xiaoting Wu, Fang Xie, Ilya D. Gridnev, Wanbin Zhang

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

An efficient copper-catalyzed reductive defluorination of β-trifluoromethylated enones via an oxidative homocoupling of Grignard reagents is reported. The reaction proceeded smoothly with a wide range of substrates, including the ones bearing aromatic heterocycles, such as furyl and thienyl ring systems in high yields (80-92%, except one example) under mild conditions. This provides a practical method for synthesis of gem-difluoroolefin ketones. It is also worth noting that this homocoupling process of Grignard reagents using β-trifluoromethylated enones as "oxidizing reagents" is effective for both the Csp2-Csp2 and Csp3-Csp3 bond formations, including for substrates whose β-hydride elimination of the corresponding transition metal alkyl complex is particularly facile, affording coupling products with high yields (83-95%), simultaneously.

Original languageEnglish
Pages (from-to)1638-1642
Number of pages5
JournalOrganic letters
Volume20
Issue number6
DOIs
Publication statusPublished - 2018 Mar 16

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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