Palladium-catalyzed regio- and stereoselective chlorothiolation of terminal alkynes with sulfenyl chlorides

Masayuki Iwasaki, Tomoya Fujii, Arisa Yamamoto, Kiyohiko Nakajima, Yasushi Nishihara

Research output: Contribution to journalArticle

40 Citations (Scopus)

Abstract

Chlorothiolation of terminal alkynes with sulfenyl chlorides yields anti-adducts without transition-metal catalysts. In sharp contrast, transition-metal-catalyzed chlorothiolation has not been developed to date, possibly because organosulfur compounds can poison catalyst. Herein, the regio- and stereoselective palladium-catalyzed chlorothiolation of terminal alkynes with sulfenyl chlorides is described. syn-Chlorothiolation offers a complementary synthetic route to chloroalkenyl sulfides. 2-Chloroalkenyl sulfides can easily be transformed into various sulfur-containing products, most of which are often found in natural products and pharmaceuticals.

Original languageEnglish
Pages (from-to)58-62
Number of pages5
JournalChemistry - An Asian Journal
Volume9
Issue number1
DOIs
Publication statusPublished - Jan 1 2014

Keywords

  • addition
  • alkynes
  • chlorothiolation
  • homogeneous catalysis
  • palladium

ASJC Scopus subject areas

  • Chemistry(all)
  • Biochemistry
  • Organic Chemistry

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