Palladium-catalyzed cross-coupling reactions with fluorinated substrates: Mechanistic insights into the undesired hydrodehalogenation of aryl halides

Meital Orbach, Joyanta Choudhury, Michal Lahav, Olena V. Zenkina, Yael Diskin-Posner, Gregory Leitus, Mark A. Iron, Milko E. Van Der Boom

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11 Citations (Scopus)

Abstract

We report here that the undesired hydrodehalogenation in cross-coupling reactions with fluorinated substrates involves water as a possible hydrogen source. Moreover, the product distribution (hydrodehalogenation vs carbon-carbon coupling) can be controlled by varying the phosphine substituents. Significant hydrodehalogenation occurs prior to the formation of Ar F-Pd(II)-Br complexes. DFT calculations were used to evaluate a direct hydrodehalogenation route with a phosphine and water. These findings provide new mechanistic insight into aryl-Br bond activation with fluorinated substrates and selective arene functionalization.

Original languageEnglish
Pages (from-to)1271-1274
Number of pages4
JournalOrganometallics
Volume31
Issue number4
DOIs
Publication statusPublished - Feb 27 2012

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ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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