Synthesis of Functionalized Vinylsilanes via Metal-Free Dehydrogenative Silylation of Enamides
A novel method of metal-free dehydrogenative silylation of enamides has been developed. The desired functionalized vinylsilane products were obtained in moderate to good yield and with high stereoselectivities. This protocol displays good tolerance of various functionalities. Furthermore, the high c...
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Veröffentlicht in: | Organic letters 2020-02, Vol.22 (4), p.1326-1330 |
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creator | Chang, Xi-Hao Wang, Zi-Lu Zhao, Meng Yang, Chao Li, Jie-Jun Ma, Wei-Wei Xu, Yun-He |
description | A novel method of metal-free dehydrogenative silylation of enamides has been developed. The desired functionalized vinylsilane products were obtained in moderate to good yield and with high stereoselectivities. This protocol displays good tolerance of various functionalities. Furthermore, the high chemoselectivity of this reaction enables us to introduce different unsaturated C–C moieties to the products. The ease of further derivatization of the products to other useful compounds also demonstrates the highly synthetic utility of the current methodology. |
doi_str_mv | 10.1021/acs.orglett.9b04645 |
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The desired functionalized vinylsilane products were obtained in moderate to good yield and with high stereoselectivities. This protocol displays good tolerance of various functionalities. Furthermore, the high chemoselectivity of this reaction enables us to introduce different unsaturated C–C moieties to the products. 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Lett</addtitle><description>A novel method of metal-free dehydrogenative silylation of enamides has been developed. The desired functionalized vinylsilane products were obtained in moderate to good yield and with high stereoselectivities. This protocol displays good tolerance of various functionalities. Furthermore, the high chemoselectivity of this reaction enables us to introduce different unsaturated C–C moieties to the products. The ease of further derivatization of the products to other useful compounds also demonstrates the highly synthetic utility of the current methodology.</description><subject>Chemistry</subject><subject>Chemistry, Organic</subject><subject>Physical Sciences</subject><subject>Science & Technology</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>AOWDO</sourceid><recordid>eNqNkc1u1DAURi0Eoj_wBEgoSySUqa_tOOMlGjoFqYhFgSWR7dy0rjx2iZ2i8PQ4zDBLxMpX1vmuPx0T8groCiiDC23TKo63HnNeKUOFFM0TcgoN43VLG_b0OEt6Qs5SuqcUyo16Tk44KKWEZKfk-80c8h0ml6o4VNsp2Oxi0N79wr765sLsk_M6YKoena4-Yda-3o6I1Xu8m_sx3mLQ2T1ideP87PUSXhZdBr1zPaYX5NmgfcKXh_OcfN1eftl8qK8_X33cvLuutQDIteCGD20rGa6BNYKZwUijRC96tEYzyhvbAkNJFcfGKJCDtKhlDxYAGQI_J2_2ex_G-GPClLudSxb9Uj1OqWO8oVStpRAF5XvUjjGlEYfuYXQ7Pc4d0G4R2xWx3UFsdxBbUq8PD0xmh_0x89dkAdZ74CeaOCTrMFg8YpTSBqSULSsTg43Lf1Rt4hRyib79_2ihL_b0UvM-TmP5rfTP7r8BZX-pew</recordid><startdate>20200221</startdate><enddate>20200221</enddate><creator>Chang, Xi-Hao</creator><creator>Wang, Zi-Lu</creator><creator>Zhao, Meng</creator><creator>Yang, Chao</creator><creator>Li, Jie-Jun</creator><creator>Ma, Wei-Wei</creator><creator>Xu, Yun-He</creator><general>American Chemical Society</general><general>Amer Chemical Soc</general><scope>1KM</scope><scope>1KN</scope><scope>AOWDO</scope><scope>BLEPL</scope><scope>DTL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-8817-0626</orcidid></search><sort><creationdate>20200221</creationdate><title>Synthesis of Functionalized Vinylsilanes via Metal-Free Dehydrogenative Silylation of Enamides</title><author>Chang, Xi-Hao ; Wang, Zi-Lu ; Zhao, Meng ; Yang, Chao ; Li, Jie-Jun ; Ma, Wei-Wei ; Xu, Yun-He</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a411t-43b3f7762e812542bfb6b94d4decba2035c712e6093e5b916f6cea6d1c11e2e13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Chemistry</topic><topic>Chemistry, Organic</topic><topic>Physical Sciences</topic><topic>Science & Technology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Chang, Xi-Hao</creatorcontrib><creatorcontrib>Wang, Zi-Lu</creatorcontrib><creatorcontrib>Zhao, Meng</creatorcontrib><creatorcontrib>Yang, Chao</creatorcontrib><creatorcontrib>Li, Jie-Jun</creatorcontrib><creatorcontrib>Ma, Wei-Wei</creatorcontrib><creatorcontrib>Xu, Yun-He</creatorcontrib><collection>Index Chemicus</collection><collection>Current Chemical Reactions</collection><collection>Web of Science - Science Citation Index Expanded - 2020</collection><collection>Web of Science Core Collection</collection><collection>Science Citation Index Expanded</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Chang, Xi-Hao</au><au>Wang, Zi-Lu</au><au>Zhao, Meng</au><au>Yang, Chao</au><au>Li, Jie-Jun</au><au>Ma, Wei-Wei</au><au>Xu, Yun-He</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Functionalized Vinylsilanes via Metal-Free Dehydrogenative Silylation of Enamides</atitle><jtitle>Organic letters</jtitle><stitle>ORG LETT</stitle><addtitle>Org. Lett</addtitle><date>2020-02-21</date><risdate>2020</risdate><volume>22</volume><issue>4</issue><spage>1326</spage><epage>1330</epage><pages>1326-1330</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A novel method of metal-free dehydrogenative silylation of enamides has been developed. The desired functionalized vinylsilane products were obtained in moderate to good yield and with high stereoselectivities. This protocol displays good tolerance of various functionalities. Furthermore, the high chemoselectivity of this reaction enables us to introduce different unsaturated C–C moieties to the products. The ease of further derivatization of the products to other useful compounds also demonstrates the highly synthetic utility of the current methodology.</abstract><cop>WASHINGTON</cop><pub>American Chemical Society</pub><pmid>31999462</pmid><doi>10.1021/acs.orglett.9b04645</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0001-8817-0626</orcidid></addata></record> |
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subjects | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
title | Synthesis of Functionalized Vinylsilanes via Metal-Free Dehydrogenative Silylation of Enamides |
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