Ruthenium-catalyzed arylation of fluorinated aromatic ketones via ortho-selective carbon-fluorine bond cleavage

Keisuke Kawamoto, Takuya Kochi, Mitsuo Sato, Eiichiro Mizushima, Fumitoshi Kakiuchi

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

We report here ruthenium-catalyzed arylation of fluorinated aromatic ketones via ortho-selective carbon-fluorine bond cleavage. In the presence of trimethylvinylsilane and cesium fluoride, ortho carbon-fluoride bonds of aromatic ketones were phenylated by 5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane using RuH2(CO)(PPh3)3 as a catalyst. Tandem C-F phenylation/C-H alkylation was observed for substrates bearing both one ortho hydrogen and one ortho fluorine atoms

Original languageEnglish
Pages (from-to)5888-5890
Number of pages3
JournalTetrahedron Letters
Volume52
Issue number44
DOIs
Publication statusPublished - 2011 Nov 2

Keywords

  • Arylation
  • Arylboronates
  • Carbon-fluorine bond cleavage
  • Ruthenium catalyst
  • Tandem arylation/alkylation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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