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Addition of unactivated thiols to epoxides and oxetanes catalyzed by a rhenium-oxo complex
Affiliation:1. University of Strasbourg, Institute Charles Sadron, CNRS UPR 22, 23, rue du Loess, 67034 Strasbourg, France;2. Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena, Humboldtstraße 10, 07743 Jena, Germany;3. Jena Center for Soft Matter (JCSM), Friedrich Schiller University Jena, Philosophenweg 7, 07743 Jena, Germany;4. Dutch Polymer Institute (DPI), P.O. Box 902, 5600 AX Eindhoven, The Netherlands;1. School of Materials Science and Engineering, East China University of Science and Technology, 200237 Shanghai, China;2. School of Materials Science and Engineering, University of Shanghai for Science and Technology, 200093 Shanghai, China;1. School of Chemistry and Chemical Engineering, University of Jinan, 336 West Nanxinzhuang Road, 250022 Jinan, PR China;2. Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, PR China;3. Department of Chemistry, New York University, 100 Washington Square East, New York, NY 10003, USA;1. N. I. Pirogov Russian National Research Medical University (RNRMU), 117997 Moscow, Russian Federation;2. Sandoz Pharmaceutical, 125315 Moscow, Russian Federation;1. Key Laboratory of Medicinal Chemistry for Natural Resources (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, PR China;2. Department of Chemistry and Biomedical Engineering, Boston University, Boston, MA 02215, USA;3. Advanced Analysis and Measurement Center, Yunnan University, Kunming, 650091, PR China
Abstract:A method for synthesizing β- and γ-hydroxy thioethers via addition of unactivated thiols to epoxides and oxetanes has been developed. This reaction is proposed to proceed through an unconventional mode of activation of the heterocycles. The transformation is catalyzed by ReO2I(PPh3)2 affording β- and γ-hydroxy thioethers in moderate to excellent yield with excellent regioselectivity.
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