Selective and scalable synthesis of trifluoromethanesulfenamides and fluorinated unsymmetrical disulfides using a shelf-stable electrophilic SCF3 reagent

Roman Pluta, Magnus Rueping*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

32 Scopus citations

Abstract

The chemoselective trifluoromethylthiolation of nitrogen nucleophiles and thiols using N-(trifluorome-thylthio)phthalimide under mild, metal-free conditions is described. A series of trifluoromethanesulfenamides and unsymmetrical disulfides is prepared from the corresponding aliphatic and aromatic amines and thiols in good yields. The reactions are operationally simple and tolerate a wide variety of functional groups. Trifluoromethanesulfenamides and disulfides belong to interesting classes of organic molecules which possess remarkable properties for medicinal and agrochemical applications.

Original languageEnglish (US)
Pages (from-to)17315-17318
Number of pages4
JournalChemistry - A European Journal
Volume20
Issue number52
DOIs
StatePublished - Dec 22 2014
Externally publishedYes

Keywords

  • Fluorine
  • S-N bond formation
  • Sulfenamides
  • Synthetic methods
  • Trifluoromethanesulfenylation

ASJC Scopus subject areas

  • Chemistry(all)

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