Synthesis of Active Hexafluoroisopropyl Benzoates through a Hydrogen-Bond-Enabled Palladium(II)-Catalyzed C−H Alkoxycarbonylation Reaction

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A PdII-catalyzed ortho C−H alkoxycarbonylation reaction of aryl silanes toward active hexafluoroisopropyl (HFIP) benzoate esters has been developed. This efficient reaction features high selectivity and good functional-group tolerance. Notably, given the general nature of the silyl-tethered directing group, this method delivers products bearing two independently modifiable sites. NMR studies reveal the presence of hydrogen bonding between HFIP and a pyrimidine nitrogen atom of the directing group, and it is thought to be crucial for the success of this alkoxycarbonylation reaction.

Original languageEnglish (US)
Pages (from-to)3191-3195
Number of pages5
JournalAngewandte Chemie - International Edition
Issue number12
Publication statusPublished - Jan 1 2017
Externally publishedYes



  • C−H activation
  • heterocycles
  • hydrogen bonds
  • palladium
  • silane

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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