Nickel-Catalyzed Cross-Electrophile Coupling Reactions for the Synthesis of gem-Difluorovinyl Arenes

Baojian Xiong, Ting Wang, Haotian Sun, Yue Li, Søren Kramer, Gui Juan Cheng, Zhong Lian*

*Corresponding author for this work

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

A nickel-catalyzed cross-electrophile coupling reaction between (hetero)aryl bromides and 2,2-difluorovinyl tosylate is presented. This protocol provides facile incorporation of the gem-difluorovinyl moiety in organic molecules. The method features mild reaction conditions, good functional group tolerance, and excellent yields. Furthermore, mechanistic experiments and DFT studies indicate a Ni(0)/Ni(II) catalytic cycle, thus differing from the currently accepted catalytic cycle for nickel-catalyzed C(sp2)-C(sp2) cross-electrophile coupling reactions.

Original languageEnglish
JournalACS Catalysis
Volume10
Issue number22
Pages (from-to)13616-13623
ISSN2155-5435
DOIs
Publication statusPublished - 2020

Keywords

  • 2,2-difluorovinyl tosylate
  • cross-electrophile coupling
  • DFT studies
  • gem-difluoroalkenes
  • nickel catalysis

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