Visible light-promoted metal-free C-H activation: Diarylketone-catalyzed selective benzylic mono- and difluorination

Ji Bao Xia, Chen Zhu, Chuo Chen

Research output: Contribution to journalArticle

267 Citations (Scopus)

Abstract

We report herein an operationally simple method for the direct conversion of benzylic C-H groups to C-F. We show that visible light can activate diarylketones to abstract a benzylic hydrogen atom selectively. Adding a fluorine radical donor yields the benzylic fluoride and regenerates the catalyst. The selective formation of mono- and difluorination products can be achieved by catalyst control. 9-Fluorenone catalyzes benzylic C-H monofluorination, while xanthone catalyzes benzylic C-H difluorination. The scope and efficiency of this new C-H fluorination method are significantly better than those of the existing methods. This is also the first report of selective C-H gem-difluorination.

Original languageEnglish (US)
Pages (from-to)17494-17500
Number of pages7
JournalJournal of the American Chemical Society
Volume135
Issue number46
DOIs
StatePublished - Nov 20 2013

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Light Metals
Light metals
Chemical activation
Gems
Light
Fluorination
Catalysts
Fluorine
Fluorides
Hydrogen
Halogenation
Atoms

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Visible light-promoted metal-free C-H activation : Diarylketone-catalyzed selective benzylic mono- and difluorination. / Xia, Ji Bao; Zhu, Chen; Chen, Chuo.

In: Journal of the American Chemical Society, Vol. 135, No. 46, 20.11.2013, p. 17494-17500.

Research output: Contribution to journalArticle

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