Palladium‐Catalyzed Regio‐ and Stereoselective Chlorothiolation of Terminal Alkynes with Sulfenyl Chlorides |
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Authors: | Dr Masayuki Iwasaki Tomoya Fujii Arisa Yamamoto Prof?Dr Kiyohiko Nakajima Prof?Dr Yasushi Nishihara |
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Institution: | 1. Division of Earth, Life, and Molecular Sciences, Graduate School of Natural Science and Technology, 3‐1‐1 Tsushimanaka, Kita‐ku, Okayama 700‐8530 (Japan), Fax: (+81)?86‐251‐7855;2. Department of Chemistry, Aichi University of Education, Igaya, Kariya 448‐8542 (Japan) |
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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. |
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Keywords: | addition alkynes chlorothiolation homogeneous catalysis palladium |
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