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Asymmetric synthesis of allylic sulfides via palladium-mediated allylation of thiols
Affiliation:1. Chemistry Department, Faculty of Science, Islamic University of Gaza, PO Box 108, Gaza Strip, Palestine;2. Chemistry Department, Faculty of Science, Al-Azhar University, PO Box 1277, Gaza, Palestine;3. UMET, UMR CNRS N°8207, Université Lille 1—Sciences et Technologies, 59655 Villeneuve d’Ascq Cedex, France;4. Chemistry Department, Faculty of Applied Science, Alaqsa University, PO Box 4051, Gaza, Palestine;5. Medical Laboratory Sciences Department, Faculty of Health Science, Islamic University of Gaza, PO Box 108, Gaza Strip, Palestine;6. School of Chemistry, The University of Manchester, Brunswick Street, Manchester M13 9PL, United Kingdom;7. Manchester Institute of Biotechnology, School of Chemistry and EPS, The University of Manchester, Manchester M1 7DN, United Kingdom;1. School of Physical Sciences, The Open University, Walton Hall, Milton Keynes, MK7 6AA, UK;2. Laboratório de Colisões Atómicas e Moleculares, CEFITEC, Departamento de Física, FCT - Universidade NOVA de Lisboa, P-2829-516, Caparica, Portugal;3. CEA/CNRS/ENSICAEN/Université de Caen Normandie) Boulevard Becquerel, 14070 Caen, France;4. School of Physical Sciences, Ingram Building, University of Kent, Canterbury, CT2 7NH, UK;1. Department of Chemistry, College of Science, King Saud University, Riyadh, Saudi Arabia;2. Department of Chemistry, College of Science & General Studies, Alfaisal University, Riyadh, Saudi Arabia;1. Department of Chemistry and Biomolecular Science, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan;2. Dai-ichi Kogyo Seiyaku Co., Ltd, 5 Oogawara-cho, Kisshoin, Minami-ku, Kyoto 601-8391, Japan;3. Environmental and Renewable Energy System Division, Graduate School of Engineering, 1-1, Yanagido, Gifu University, Gifu 501-1193, Japan;1. State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123, Jiangsu, PR China;2. NanJing YuTong Experimental School, Nanjing, 211100, Jiangsu, PR China;3. Faculty of Science, Health, Education and Engineering, University of the Sunshine Coast, Maroochydore, Queensland, 4558, Australia;4. Applied Technology College of Soochow University, Suzhou, 215325, Jiangsu, PR China
Abstract:Cyclic and acyclic allylic S-p-chlorophenyl, S-2-pyridyl and S-2-pyrimidyl sulfides of 50–96% ee have been obtained in 24–87% yield through reaction of the corresponding racemic carbonates with p-chlorothiophenol, 2-mercaptopyridine and 2-mercaptopyrimidine, respectively, mediated by a complex generated in situ from Pd2(dba)3·CHCl3 and the Trost ligand.
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