Nickel-Catalyzed Decarbonylative Synthesis of Fluoroalkyl Thioethers

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

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

Abstract

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
Volume10
Issue number15
DOIs
StatePublished - Aug 7 2020
Externally publishedYes

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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