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

36 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 2014

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Alkynes
Palladium
Sulfides
Transition metals
Chlorides
Metals
Catalysts
Poisons
Biological Products
Sulfur
Pharmaceutical Preparations

Keywords

  • addition
  • alkynes
  • chlorothiolation
  • homogeneous catalysis
  • palladium

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Palladium-catalyzed regio- and stereoselective chlorothiolation of terminal alkynes with sulfenyl chlorides. / Iwasaki, Masayuki; Fujii, Tomoya; Yamamoto, Arisa; Nakajima, Kiyohiko; Nishihara, Yasushi.

In: Chemistry - An Asian Journal, Vol. 9, No. 1, 01.2014, p. 58-62.

Research output: Contribution to journalArticle

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