Deuterium-Labeling Studies on the C-H/Olefin Coupling of Aromatic Ketones Catalyzed by Fe(PMe 3) 4

Naoki Kimura, Shiori Katta, Yoichi Kitazawa, Takuya Kochi, Fumitoshi Kakiuchi

Research output: Contribution to journalArticlepeer-review

Abstract

Deuterium-labeling experiments were performed for the Fe(PMe 3) 4-catalyzed C-H/olefin coupling using a deuterium-labeled aromatic ketone with various alkenes. While the reactions with a variety of alkenes provided the linear alkylation products formed via 1,2-insertion of alkene into an Fe-H bond, the reversible 2,1-insertion proceeded during the reaction highly depends on the choice of the alkene. No H/D scrambling resulting from 2,1-insertion/β-elimination was detected for the reactions with a vinylsilane and N -vinylcarbazole, but the reactions with styrenes are considered to involve rapid 2,1-insertion/ β-elimination processes to cause significant levels of H/D scrambling.

Original languageEnglish
JournalSynthesis (Germany)
DOIs
Publication statusAccepted/In press - 2021

Keywords

  • C-H/olefin coupling
  • deuterium-labeling experiments
  • iron catalyst
  • mechanism
  • styrene

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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