Copper-Catalyzed Trifluoromethylation and Cyclization of Aromatic-Sulfonyl-Group-Tethered Alkenes for the Construction of 1,2-Benzothiazinane Dioxide Type Compounds
A multi‐talented system: An efficient copper‐catalyzed tandem trifluoromethylation/annulation of an electron‐deficient aromatic ring has been developed. This method provides a powerful and straightforward way to synthesize trifluoromethylated 1,2‐benzothiazinane dioxides under mild conditions (see s...
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Veröffentlicht in: | Chemistry : a European journal 2013-12, Vol.19 (50), p.16910-16915 |
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container_title | Chemistry : a European journal |
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creator | Dong, Xiang Sang, Rui Wang, Qiang Tang, Xiang-Ying Shi, Min |
description | A multi‐talented system: An efficient copper‐catalyzed tandem trifluoromethylation/annulation of an electron‐deficient aromatic ring has been developed. This method provides a powerful and straightforward way to synthesize trifluoromethylated 1,2‐benzothiazinane dioxides under mild conditions (see scheme). The mechanism was investigated by a series of kinetic experiments and isotopic labeling studies. |
doi_str_mv | 10.1002/chem.201303623 |
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This method provides a powerful and straightforward way to synthesize trifluoromethylated 1,2‐benzothiazinane dioxides under mild conditions (see scheme). The mechanism was investigated by a series of kinetic experiments and isotopic labeling studies.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201303623</identifier><identifier>PMID: 24194478</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Alkenes ; Alkenes - chemistry ; Aromatic compounds ; benzothiazinane ; Catalysis ; Chemical reactions ; Chemistry ; Construction ; copper ; Copper - chemistry ; Cyclization ; Dioxides ; homogeneous catalysis ; Isotopic labeling ; Molecular Structure ; Organic chemistry ; radicals ; Thiazines - chemistry ; trifluoromethylation</subject><ispartof>Chemistry : a European journal, 2013-12, Vol.19 (50), p.16910-16915</ispartof><rights>Copyright © 2013 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5473-5cba1b04f916771a2d1ba840a6064cd155d8ee76fd850bd5f2a9f4c5722520a73</citedby><cites>FETCH-LOGICAL-c5473-5cba1b04f916771a2d1ba840a6064cd155d8ee76fd850bd5f2a9f4c5722520a73</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.201303623$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201303623$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27923,27924,45573,45574</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24194478$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Dong, Xiang</creatorcontrib><creatorcontrib>Sang, Rui</creatorcontrib><creatorcontrib>Wang, Qiang</creatorcontrib><creatorcontrib>Tang, Xiang-Ying</creatorcontrib><creatorcontrib>Shi, Min</creatorcontrib><title>Copper-Catalyzed Trifluoromethylation and Cyclization of Aromatic-Sulfonyl-Group-Tethered Alkenes for the Construction of 1,2-Benzothiazinane Dioxide Type Compounds</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>A multi‐talented system: An efficient copper‐catalyzed tandem trifluoromethylation/annulation of an electron‐deficient aromatic ring has been developed. This method provides a powerful and straightforward way to synthesize trifluoromethylated 1,2‐benzothiazinane dioxides under mild conditions (see scheme). The mechanism was investigated by a series of kinetic experiments and isotopic labeling studies.</description><subject>Alkenes</subject><subject>Alkenes - chemistry</subject><subject>Aromatic compounds</subject><subject>benzothiazinane</subject><subject>Catalysis</subject><subject>Chemical reactions</subject><subject>Chemistry</subject><subject>Construction</subject><subject>copper</subject><subject>Copper - chemistry</subject><subject>Cyclization</subject><subject>Dioxides</subject><subject>homogeneous catalysis</subject><subject>Isotopic labeling</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>radicals</subject><subject>Thiazines - chemistry</subject><subject>trifluoromethylation</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkU9v0zAYhy0EYt3gyhFF4sJhLv7v5FjC1iENEKKIo-UmjurNiTM7EUs_Dx8UV9kqxGUn67We3yO__gHwBqMlRoh8qHamXRKEKaKC0GdggTnBkErBn4MFKpiEgtPiBJzGeIMQKgSlL8EJYbhgTOYL8Kf0fW8CLPWg3bQ3dbYJtnGjD741w25yerC-y3RXZ-VUObufZ99kq0SkoYI_Rtf4bnJwHfzYw02KmZBEK3drOhOzxocsXWWl7-IQxupRgM8J_Gi6vR92Vu9tpzuTfbL-3tYm20z9IdD2fuzq-Aq8aLSL5vXDeQZ-Xl5syit4_W39uVxdw4ozSSGvthpvEWsKLKTEmtR4q3OGtECCVTXmvM6NkaKpc462NW-ILhpWcUkIJ0hLegbez94--LvRxEG1NlbGufQ0P0aFpcxR-mjOnkaZ4LmgWOCEvvsPvfFj6NIiB4oVVGJcJGo5U1XwMQbTqD7YVodJYaQOVatD1epYdQq8fdCO29bUR_yx2wQUM_DbOjM9oVPl1cWXf-Vwzto4mPtjVodbJSSVXP36ulYF_n7JOZKK0L-Qn8ZD</recordid><startdate>20131209</startdate><enddate>20131209</enddate><creator>Dong, Xiang</creator><creator>Sang, Rui</creator><creator>Wang, Qiang</creator><creator>Tang, Xiang-Ying</creator><creator>Shi, Min</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20131209</creationdate><title>Copper-Catalyzed Trifluoromethylation and Cyclization of Aromatic-Sulfonyl-Group-Tethered Alkenes for the Construction of 1,2-Benzothiazinane Dioxide Type Compounds</title><author>Dong, Xiang ; Sang, Rui ; Wang, Qiang ; Tang, Xiang-Ying ; Shi, Min</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5473-5cba1b04f916771a2d1ba840a6064cd155d8ee76fd850bd5f2a9f4c5722520a73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Alkenes</topic><topic>Alkenes - chemistry</topic><topic>Aromatic compounds</topic><topic>benzothiazinane</topic><topic>Catalysis</topic><topic>Chemical reactions</topic><topic>Chemistry</topic><topic>Construction</topic><topic>copper</topic><topic>Copper - chemistry</topic><topic>Cyclization</topic><topic>Dioxides</topic><topic>homogeneous catalysis</topic><topic>Isotopic labeling</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>radicals</topic><topic>Thiazines - chemistry</topic><topic>trifluoromethylation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dong, Xiang</creatorcontrib><creatorcontrib>Sang, Rui</creatorcontrib><creatorcontrib>Wang, Qiang</creatorcontrib><creatorcontrib>Tang, Xiang-Ying</creatorcontrib><creatorcontrib>Shi, Min</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dong, Xiang</au><au>Sang, Rui</au><au>Wang, Qiang</au><au>Tang, Xiang-Ying</au><au>Shi, Min</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper-Catalyzed Trifluoromethylation and Cyclization of Aromatic-Sulfonyl-Group-Tethered Alkenes for the Construction of 1,2-Benzothiazinane Dioxide Type Compounds</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. 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subjects | Alkenes Alkenes - chemistry Aromatic compounds benzothiazinane Catalysis Chemical reactions Chemistry Construction copper Copper - chemistry Cyclization Dioxides homogeneous catalysis Isotopic labeling Molecular Structure Organic chemistry radicals Thiazines - chemistry trifluoromethylation |
title | Copper-Catalyzed Trifluoromethylation and Cyclization of Aromatic-Sulfonyl-Group-Tethered Alkenes for the Construction of 1,2-Benzothiazinane Dioxide Type Compounds |
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