Base-Catalyzed Stereoselective Vinylation of Ketones with Arylacetylenes: A New C(sp3)C(sp2) Bond-Forming Reaction
Alkylaryl‐ and alkylheteroarylketones, including those with condensed aromatic moieties, are readily vinylated with arylacetylenes (KOH/DMSO, 100 °C, 1 h) to give regio‐ and stereoselectively the (E)‐β‐γ‐ethylenic ketones ((E)‐3‐buten‐1‐ones) in 61–84 % yields and with approximately 100 % stereosele...
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| Veröffentlicht in: | Chemistry : a European journal 2010-07, Vol.16 (28), p.8516-8521 |
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| container_title | Chemistry : a European journal |
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| creator | Trofimov, Boris A. Schmidt, Elena Yu Ushakov, Igor' A. Zorina, Nadezhda V. Skital'tseva, Elena V. Protsuk, Nadezhda I. Mikhaleva, Al'bina I. |
| description | Alkylaryl‐ and alkylheteroarylketones, including those with condensed aromatic moieties, are readily vinylated with arylacetylenes (KOH/DMSO, 100 °C, 1 h) to give regio‐ and stereoselectively the (E)‐β‐γ‐ethylenic ketones ((E)‐3‐buten‐1‐ones) in 61–84 % yields and with approximately 100 % stereoselectivity. This vinylation represents a new C(sp3)C(sp2) bond‐forming reaction of high synthetic potential.
A valuable vinylation! Previously unknown C‐vinylation of ketones occurs with high E stereoselectivity and excellent yields when alkylaryl‐ and alkylheteroarylketones are treated with arylacetylenes in the presence of KOH/DMSO at 100 °C. This represents a new C(sp3)C(sp2) bond‐forming reaction of wide scope (see scheme). |
| doi_str_mv | 10.1002/chem.201000227 |
| format | Article |
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A valuable vinylation! Previously unknown C‐vinylation of ketones occurs with high E stereoselectivity and excellent yields when alkylaryl‐ and alkylheteroarylketones are treated with arylacetylenes in the presence of KOH/DMSO at 100 °C. This represents a new C(sp3)C(sp2) bond‐forming reaction of wide scope (see scheme).</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201000227</identifier><identifier>PMID: 20564291</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>alkynes ; Bonding ; Chemistry ; Condensing ; CC bond formation ; Ketones ; Stereoselectivity ; superbases ; vinylation</subject><ispartof>Chemistry : a European journal, 2010-07, Vol.16 (28), p.8516-8521</ispartof><rights>Copyright © 2010 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4437-4d8706e94a24644ac5cd77c84c4fca97222949354398d3895957c5392567f09c3</citedby><cites>FETCH-LOGICAL-c4437-4d8706e94a24644ac5cd77c84c4fca97222949354398d3895957c5392567f09c3</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.201000227$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201000227$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,777,781,1412,27905,27906,45555,45556</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20564291$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Trofimov, Boris A.</creatorcontrib><creatorcontrib>Schmidt, Elena Yu</creatorcontrib><creatorcontrib>Ushakov, Igor' A.</creatorcontrib><creatorcontrib>Zorina, Nadezhda V.</creatorcontrib><creatorcontrib>Skital'tseva, Elena V.</creatorcontrib><creatorcontrib>Protsuk, Nadezhda I.</creatorcontrib><creatorcontrib>Mikhaleva, Al'bina I.</creatorcontrib><title>Base-Catalyzed Stereoselective Vinylation of Ketones with Arylacetylenes: A New C(sp3)C(sp2) Bond-Forming Reaction</title><title>Chemistry : a European journal</title><addtitle>Chemistry - A European Journal</addtitle><description>Alkylaryl‐ and alkylheteroarylketones, including those with condensed aromatic moieties, are readily vinylated with arylacetylenes (KOH/DMSO, 100 °C, 1 h) to give regio‐ and stereoselectively the (E)‐β‐γ‐ethylenic ketones ((E)‐3‐buten‐1‐ones) in 61–84 % yields and with approximately 100 % stereoselectivity. This vinylation represents a new C(sp3)C(sp2) bond‐forming reaction of high synthetic potential.
A valuable vinylation! Previously unknown C‐vinylation of ketones occurs with high E stereoselectivity and excellent yields when alkylaryl‐ and alkylheteroarylketones are treated with arylacetylenes in the presence of KOH/DMSO at 100 °C. This represents a new C(sp3)C(sp2) bond‐forming reaction of wide scope (see scheme).</description><subject>alkynes</subject><subject>Bonding</subject><subject>Chemistry</subject><subject>Condensing</subject><subject>CC bond formation</subject><subject>Ketones</subject><subject>Stereoselectivity</subject><subject>superbases</subject><subject>vinylation</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNqFkc1u1DAURiMEokNhyxJZYkG7yODfOGY3E7VTRDtIBcrSMs4NTUniwU4YwuvwIDwSr4CjKSPEAla-ss93pOsvSR4TPCcY0-f2Gto5xXHGlMo7yYwISlImM3E3mWHFZZoJpg6SByHcREZljN1PDigWGaeKzJJhaQKkhelNM36DEr3pwYML0IDt6y-ArupubExfuw65Cr2C3nUQ0Lbur9HCxxcL_dhAvHuBFmgNW1QchQ07_vn9xzTQY7R0XZmeOt_W3Ud0CcZOrofJvco0AR7dnofJu9OTt8VZev569bJYnKeWcyZTXuYSZ6C4oTzj3FhhSyltzi2vrFGSUqq4YoIzlZcsV0IJaeO6VGSywsqyw-TZzrvx7vMAoddtHSw0jenADUFLxuOfCKwiefRPkuQYc5VnYkKf_oXeuMF3cQ9NZDYRipBIzXeU9S4ED5Xe-Lo1ftQE66k6PVWn99XFwJNb7fChhXKP_-4qAmoHbOsGxv_odHF2cvGnPN1l69DD133W-E86k0wK_X690lcFWa8ulyt9wX4BbYOywQ</recordid><startdate>20100726</startdate><enddate>20100726</enddate><creator>Trofimov, Boris A.</creator><creator>Schmidt, Elena Yu</creator><creator>Ushakov, Igor' A.</creator><creator>Zorina, Nadezhda V.</creator><creator>Skital'tseva, Elena V.</creator><creator>Protsuk, Nadezhda I.</creator><creator>Mikhaleva, Al'bina I.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</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>20100726</creationdate><title>Base-Catalyzed Stereoselective Vinylation of Ketones with Arylacetylenes: A New C(sp3)C(sp2) Bond-Forming Reaction</title><author>Trofimov, Boris A. ; Schmidt, Elena Yu ; Ushakov, Igor' A. ; Zorina, Nadezhda V. ; Skital'tseva, Elena V. ; Protsuk, Nadezhda I. ; Mikhaleva, Al'bina I.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4437-4d8706e94a24644ac5cd77c84c4fca97222949354398d3895957c5392567f09c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>alkynes</topic><topic>Bonding</topic><topic>Chemistry</topic><topic>Condensing</topic><topic>CC bond formation</topic><topic>Ketones</topic><topic>Stereoselectivity</topic><topic>superbases</topic><topic>vinylation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Trofimov, Boris A.</creatorcontrib><creatorcontrib>Schmidt, Elena Yu</creatorcontrib><creatorcontrib>Ushakov, Igor' A.</creatorcontrib><creatorcontrib>Zorina, Nadezhda V.</creatorcontrib><creatorcontrib>Skital'tseva, Elena V.</creatorcontrib><creatorcontrib>Protsuk, Nadezhda I.</creatorcontrib><creatorcontrib>Mikhaleva, Al'bina I.</creatorcontrib><collection>Istex</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>Trofimov, Boris A.</au><au>Schmidt, Elena Yu</au><au>Ushakov, Igor' A.</au><au>Zorina, Nadezhda V.</au><au>Skital'tseva, Elena V.</au><au>Protsuk, Nadezhda I.</au><au>Mikhaleva, Al'bina I.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Base-Catalyzed Stereoselective Vinylation of Ketones with Arylacetylenes: A New C(sp3)C(sp2) Bond-Forming Reaction</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry - A European Journal</addtitle><date>2010-07-26</date><risdate>2010</risdate><volume>16</volume><issue>28</issue><spage>8516</spage><epage>8521</epage><pages>8516-8521</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>Alkylaryl‐ and alkylheteroarylketones, including those with condensed aromatic moieties, are readily vinylated with arylacetylenes (KOH/DMSO, 100 °C, 1 h) to give regio‐ and stereoselectively the (E)‐β‐γ‐ethylenic ketones ((E)‐3‐buten‐1‐ones) in 61–84 % yields and with approximately 100 % stereoselectivity. This vinylation represents a new C(sp3)C(sp2) bond‐forming reaction of high synthetic potential.
A valuable vinylation! Previously unknown C‐vinylation of ketones occurs with high E stereoselectivity and excellent yields when alkylaryl‐ and alkylheteroarylketones are treated with arylacetylenes in the presence of KOH/DMSO at 100 °C. This represents a new C(sp3)C(sp2) bond‐forming reaction of wide scope (see scheme).</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>20564291</pmid><doi>10.1002/chem.201000227</doi><tpages>6</tpages></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | alkynes Bonding Chemistry Condensing CC bond formation Ketones Stereoselectivity superbases vinylation |
| title | Base-Catalyzed Stereoselective Vinylation of Ketones with Arylacetylenes: A New C(sp3)C(sp2) Bond-Forming Reaction |
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