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Regioselective aerobic oxidation of bis-sulfides into monosulfoxides
Affiliation:1. Centro di Studi CNR sulle Metodologie Innovative di Sintesi Organiche M.I.S.O., Istituto di Chimica del Politecnico di Bari, trav.200 Re David, 4 I-70125 Bari, Italy;2. Centro di Studi CNR sulle Metodologie Innovative di Sintesi Organiche M.I.S.O., Dipartimento di Chimica dell''Università degli Studi di Bari, Via Orabona, 4 I-70125 Bari, Italy;1. Key Laboratory of Beijing City on Preparation and Processing of Novel Polymer Materials, Beijing University of Chemical Technology, Beijing 100029, China;2. State Key Laboratory of Organic-Inorganic Composites, Beijing University of Chemical Technology, Beijing 100029, China;1. Department of Biotechnology, Building 123, Yonsei University, 50 Yonsei-ro, Seodaemun-gu, Seoul, 03722, Republic of Korea;2. Doping Control Center, Korea Institute of Science and Technology (KIST), Hwarang-ro 14-gil 5, Seongbuk-gu, Seoul, 02792, Republic of Korea;3. Juvic Biotech. Inc., Building 102, Yonsei Engineering Research Park, 50 Yonsei-ro, Seodaemun-gu, Seoul, 03722, Republic of Korea;4. Department of Biological Chemistry, Korea University of Science and Technology (UST), 217 Gajeong-ro, Yuseong-gu, Daejeon 34113, Republic of Korea;1. Materials and Engineering Research Institute, Sheffield Hallam University, Sheffield, UK;2. Gebze Technical University, Department of Chemistry, Gebze 41400, Kocaeli, Turkey;3. Nikolaev Institutes of Inorganic Chemistry SB RAS, Lavrentiev Pr. 3, Novosibirsk 630090, Russia;4. Novosibirsk State University, Pirogova Str. 2, Russia
Abstract:The cobalt(II) acetylacetonate/aldehyde-promoted aerobic oxidation of three bis-sulfides of general formula R1-SCH2CH2S-R2, where R1 is a heterocycle and R2 is p-tolyl, provides a method to functionalise selectively the sulfur atom bonded to the p-tolyl moiety leading to the corresponding monosulfoxides. The same chemoselectivity and little diastereoisomeric excess (10%) was achieved by submitting to oxidative conditions the chiral bis-sulfide (S)-R3-SCH2CH(CH3)CH2-SR4 (R3=benzothiazolyl, R4=p-tolyl).
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