Copper-catalyzed trifluoromethyl thiolation-mild and efficient synthesis of trifluoromethyl thioethers

Magnus Rueping*, Nikita Tolstoluzhsky, Pavlo Nikolaienko

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

86 Scopus citations

Abstract

The perfluoroalkyl groups act as lipophilic electron-withdrawing groups, introducing additional unique properties in the molecules when compared to their non-fluorinated analogues. These properties are closely related to those of trifluoromethoxy (OCF3) and trifluoromethyl (CF3) groups. Initial search for conditions that could promote nucleophilic substitution showed, however, that bromides are completely inert and do not react under any conditions in which iodides showed reactivity. Due to the reduced nucleophilicity of the SCF3 anion, the coupling is considerably more difficult relative to non-fluorinated thiolate. However, to date, the direct synthesis of such significant compounds is unfortunately limited due to lack of safe, efficient, and general synthetic methods. There are few methods reported for the synthesis of vinyl trifluoromethyl thioethers with limited scope and moderate yields, the most recent one involving multistep procedures for the preparation of starting vinyl boronic acids and making use of expensive reagents in stoichiometric quantities.

Original languageEnglish (US)
Pages (from-to)14043-14046
Number of pages4
JournalChemistry - A European Journal
Volume19
Issue number42
DOIs
StatePublished - Nov 12 2013

Keywords

  • C-S bond formation
  • Copper
  • Thioethers
  • Trifluoromethyl thiolation
  • Vinyl iodide

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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