Nickel-Catalyzed Decarbonylative Synthesis of Fluoroalkyl Thioethers

Conor E. Brigham, Christian A. Malapit, Naish Lalloo, Melanie S. Sanford

Research output: Contribution to journalArticlepeer-review

42 Scopus citations


This report describes the development of a nickel-catalyzed decarbonylative reaction for the synthesis of fluoroalkyl thioethers (RFSR) from the corresponding thioesters. Readily available, inexpensive, and stable fluoroalkyl carboxylic acids (RFCO2H) serve as the fluoroalkyl (RF) source in this transformation. Stoichiometric organometallic studies reveal that RF-S bond-forming reductive elimination is a challenging step in the catalytic cycle. This led to the identification of diphenylphosphinoferrocene as the optimal ligand for this transformation. Ultimately, this method was applied to the construction of diverse fluoroalkyl thioethers (RFSR), with R = both aryl and alkyl.

Original languageEnglish (US)
Pages (from-to)8315-8320
Number of pages6
JournalACS Catalysis
Issue number15
StatePublished - Aug 7 2020
Externally publishedYes


  • decarbonylation
  • fluoroalkyl carboxylic acids
  • fluoroalkylation
  • nickel-catalysis
  • thioether synthesis

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis


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