Oxidative Thioesterification of Alkenes Mediated by 1,3‐Dibromo‐5,5‐dimethylhydantoin and DMSO for the Synthesis of α‐Ketothioesters
A simple and mild approach for the synthesis of α‐ketothioesters via 1,3‐Dibromo‐5,5‐dimethylhydantoin (DBH)/DMSO mediated oxidative thioesterification of alkenes has been developed. Various of α‐ketothioesters products were produced in moderate to good yields under metal‐free conditions. And this m...
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| Veröffentlicht in: | European journal of organic chemistry 2019-07, Vol.2019 (25), p.4056-4060 |
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| container_issue | 25 |
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| container_title | European journal of organic chemistry |
| container_volume | 2019 |
| creator | Hua, Jiawei Xu, Jiaqi Xu, Jia Zhou, Bochao Zhang, Dong Yang, Zhao Fang, Zheng Guo, Kai |
| description | A simple and mild approach for the synthesis of α‐ketothioesters via 1,3‐Dibromo‐5,5‐dimethylhydantoin (DBH)/DMSO mediated oxidative thioesterification of alkenes has been developed. Various of α‐ketothioesters products were produced in moderate to good yields under metal‐free conditions. And this method features readily available starting materials and broad substrate scope. Moreover, a plausible mechanism was proposed based on the methyl bromide captured experiment.
A simple and mild approach for the synthesis of α‐ketothioesters proceeds through an oxidative thioesterification of alkenes and DMSO in the presence of 1,3‐dibromo‐5,5‐dimethylhydantoin (DBH). |
| doi_str_mv | 10.1002/ejoc.201900585 |
| format | Article |
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A simple and mild approach for the synthesis of α‐ketothioesters proceeds through an oxidative thioesterification of alkenes and DMSO in the presence of 1,3‐dibromo‐5,5‐dimethylhydantoin (DBH).</description><subject>Alkenes</subject><subject>Methyl bromide</subject><subject>Oxidation</subject><subject>Substrates</subject><subject>Synthesis</subject><subject>Synthetic methods</subject><subject>Thioesterification</subject><subject>Thioesters</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFUEtOwzAQjRBIlMKWtSW2pIztOI2XqPw_ygKQ2EVJPFFc0hjsFMiOCyBxFS7CITgJrspnyWbeaPQ-mhcE2xRGFIDt4dSUIwZUAohErAQDClKGEEtY9XvEo5BKfrsebDg3BQAZx3QQvKbPWuWdfkRyXWuDrkOrK136k2mJqch-c4ctOnKJSucdKlL0hO7yz5e3A11YMzN-E7vCT6Vn2NV9U_cqbzujW5K3ihxcXqWkMpZ0NZKrvvXgtFs4f7x70Tl2pvsJdpvBWpU3Dre-cRjcHB1eT07Ci_T4dLJ_EZacjkWIoJAzERXAWUz98zjGhCdlWUQ0LySKGCTDqBI0EglIz66KSEnBMIdElRUfBjtL33trHuY-O5uauW19ZMaYYABcxuBZoyWrtMY5i1V2b_Ust31GIVtUni0qz34r9wK5FDzpBvt_2NnhWTr5034B-caLXA</recordid><startdate>20190707</startdate><enddate>20190707</enddate><creator>Hua, Jiawei</creator><creator>Xu, Jiaqi</creator><creator>Xu, Jia</creator><creator>Zhou, Bochao</creator><creator>Zhang, Dong</creator><creator>Yang, Zhao</creator><creator>Fang, Zheng</creator><creator>Guo, Kai</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-0013-3263</orcidid></search><sort><creationdate>20190707</creationdate><title>Oxidative Thioesterification of Alkenes Mediated by 1,3‐Dibromo‐5,5‐dimethylhydantoin and DMSO for the Synthesis of α‐Ketothioesters</title><author>Hua, Jiawei ; Xu, Jiaqi ; Xu, Jia ; Zhou, Bochao ; Zhang, Dong ; Yang, Zhao ; Fang, Zheng ; Guo, Kai</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3175-e0de3254b03261100e7e838ccb41ab9e56092e4f51458090defb4d952ea08dcf3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Alkenes</topic><topic>Methyl bromide</topic><topic>Oxidation</topic><topic>Substrates</topic><topic>Synthesis</topic><topic>Synthetic methods</topic><topic>Thioesterification</topic><topic>Thioesters</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hua, Jiawei</creatorcontrib><creatorcontrib>Xu, Jiaqi</creatorcontrib><creatorcontrib>Xu, Jia</creatorcontrib><creatorcontrib>Zhou, Bochao</creatorcontrib><creatorcontrib>Zhang, Dong</creatorcontrib><creatorcontrib>Yang, Zhao</creatorcontrib><creatorcontrib>Fang, Zheng</creatorcontrib><creatorcontrib>Guo, Kai</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hua, Jiawei</au><au>Xu, Jiaqi</au><au>Xu, Jia</au><au>Zhou, Bochao</au><au>Zhang, Dong</au><au>Yang, Zhao</au><au>Fang, Zheng</au><au>Guo, Kai</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Oxidative Thioesterification of Alkenes Mediated by 1,3‐Dibromo‐5,5‐dimethylhydantoin and DMSO for the Synthesis of α‐Ketothioesters</atitle><jtitle>European journal of organic chemistry</jtitle><date>2019-07-07</date><risdate>2019</risdate><volume>2019</volume><issue>25</issue><spage>4056</spage><epage>4060</epage><pages>4056-4060</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>A simple and mild approach for the synthesis of α‐ketothioesters via 1,3‐Dibromo‐5,5‐dimethylhydantoin (DBH)/DMSO mediated oxidative thioesterification of alkenes has been developed. Various of α‐ketothioesters products were produced in moderate to good yields under metal‐free conditions. And this method features readily available starting materials and broad substrate scope. Moreover, a plausible mechanism was proposed based on the methyl bromide captured experiment.
A simple and mild approach for the synthesis of α‐ketothioesters proceeds through an oxidative thioesterification of alkenes and DMSO in the presence of 1,3‐dibromo‐5,5‐dimethylhydantoin (DBH).</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.201900585</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-0013-3263</orcidid></addata></record> |
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| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Alkenes Methyl bromide Oxidation Substrates Synthesis Synthetic methods Thioesterification Thioesters |
| title | Oxidative Thioesterification of Alkenes Mediated by 1,3‐Dibromo‐5,5‐dimethylhydantoin and DMSO for the Synthesis of α‐Ketothioesters |
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