Journal
CHEMISTRY-AN ASIAN JOURNAL
Volume 9, Issue 1, Pages 58-62Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201301295
Keywords
addition; alkynes; chlorothiolation; homogeneous catalysis; palladium
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Funding
- Okayama Foundation for Natural Sciences and Technology
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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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