Alkylation of thiols with trichloroacetimidates under neutral conditions

Brian C. Duffy, Kyle T. Howard, John D. Chisholm

Research output: Contribution to journalArticle

16 Scopus citations

Abstract

Trichloroacetimidates are displaced with thiols to form the corresponding sulfides without the need for an added acid or base by simply heating the reactants in refluxing THF. This operationally simple procedure provides the corresponding sulfides in excellent yields with only the formation of the neutral trichloroacetamide as the side product. The imidate may also be formed in situ, allowing for a direct method for the formation of sulfides from alcohols. This reaction provides a general method for the synthesis of a variety of sulfides from inexpensive and readily available alcohol starting materials.

Original languageEnglish (US)
Pages (from-to)3301-3305
Number of pages5
JournalTetrahedron Letters
Volume56
Issue number23
DOIs
StatePublished - Jun 3 2015

Keywords

  • Alkylation
  • Substitution
  • Sulfide
  • Thiol
  • Trichloroacetimidate

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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