Copper-catalyzed C(sp2)-C(sp) Sonogashira-type cross-coupling reactions accelerated by polycyclic aromatic hydrocarbons
Copper‐catalyzed Sonogashira‐type reactions were dramatically accelerated by introducing a catalytic amount of polycyclic aromatic hydrocarbon additive. This novel catalytic system features low copper loading (0.5 mol% < Cu < 5 mol%), broad reaction scope and remarkable substrate tolerance. Bo...
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| Veröffentlicht in: | Applied organometallic chemistry 2015-06, Vol.29 (6), p.353-356 |
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| container_title | Applied organometallic chemistry |
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| creator | Xu, Wei Yu, Bo Sun, Huaming Zhang, Guofang Zhang, Weiqiang Gao, Ziwei |
| description | Copper‐catalyzed Sonogashira‐type reactions were dramatically accelerated by introducing a catalytic amount of polycyclic aromatic hydrocarbon additive. This novel catalytic system features low copper loading (0.5 mol% < Cu < 5 mol%), broad reaction scope and remarkable substrate tolerance. Both aromatic and aliphatic terminal alkynes as well as diverse aryl iodides were employed in this transformation, affording respectable yields of the desired products. The novel Cu(OTf)2/pyrene system was subsequently employed to synthesize phenylacetylene‐based fluorescent compounds. Copyright © 2015 John Wiley & Sons, Ltd.
A novel Cu(OTf)2/pyrene system can catalyze effectively Sonogashira‐type cross‐coupling reactions, featuring low copper loading (Cu < 5 mol%), broad reaction scope and remarkable substrate tolerance. |
| doi_str_mv | 10.1002/aoc.3298 |
| format | Article |
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A novel Cu(OTf)2/pyrene system can catalyze effectively Sonogashira‐type cross‐coupling reactions, featuring low copper loading (Cu < 5 mol%), broad reaction scope and remarkable substrate tolerance.</description><identifier>ISSN: 0268-2605</identifier><identifier>EISSN: 1099-0739</identifier><identifier>DOI: 10.1002/aoc.3298</identifier><language>eng</language><publisher>Blackwell Publishing Ltd</publisher><subject>Catalysis ; Catalysts ; Chemical compounds ; Copper ; copper catalysis ; Iodides ; Polycyclic aromatic hydrocarbons ; Pyrenes ; Sonogashira-type cross-coupling reaction ; Terminals ; Tolerances</subject><ispartof>Applied organometallic chemistry, 2015-06, Vol.29 (6), p.353-356</ispartof><rights>Copyright © 2015 John Wiley & Sons, Ltd.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5428-b9c630c2d9f5654df9b31bce2e9b79bbcc91317e548a5bc1f7a685c2dc1e52eb3</citedby><cites>FETCH-LOGICAL-c5428-b9c630c2d9f5654df9b31bce2e9b79bbcc91317e548a5bc1f7a685c2dc1e52eb3</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%2Faoc.3298$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Faoc.3298$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Xu, Wei</creatorcontrib><creatorcontrib>Yu, Bo</creatorcontrib><creatorcontrib>Sun, Huaming</creatorcontrib><creatorcontrib>Zhang, Guofang</creatorcontrib><creatorcontrib>Zhang, Weiqiang</creatorcontrib><creatorcontrib>Gao, Ziwei</creatorcontrib><title>Copper-catalyzed C(sp2)-C(sp) Sonogashira-type cross-coupling reactions accelerated by polycyclic aromatic hydrocarbons</title><title>Applied organometallic chemistry</title><addtitle>Appl. Organometal. Chem</addtitle><description>Copper‐catalyzed Sonogashira‐type reactions were dramatically accelerated by introducing a catalytic amount of polycyclic aromatic hydrocarbon additive. This novel catalytic system features low copper loading (0.5 mol% < Cu < 5 mol%), broad reaction scope and remarkable substrate tolerance. Both aromatic and aliphatic terminal alkynes as well as diverse aryl iodides were employed in this transformation, affording respectable yields of the desired products. The novel Cu(OTf)2/pyrene system was subsequently employed to synthesize phenylacetylene‐based fluorescent compounds. Copyright © 2015 John Wiley & Sons, Ltd.
A novel Cu(OTf)2/pyrene system can catalyze effectively Sonogashira‐type cross‐coupling reactions, featuring low copper loading (Cu < 5 mol%), broad reaction scope and remarkable substrate tolerance.</description><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemical compounds</subject><subject>Copper</subject><subject>copper catalysis</subject><subject>Iodides</subject><subject>Polycyclic aromatic hydrocarbons</subject><subject>Pyrenes</subject><subject>Sonogashira-type cross-coupling reaction</subject><subject>Terminals</subject><subject>Tolerances</subject><issn>0268-2605</issn><issn>1099-0739</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNp10E1P20AQBuBVRaUGWqk_wUc4LN2PrO09IgNpUShItOK4mp2Mg4uTNbuOwP31OKSi4sBp5vDo1czL2FcpjqUQ6hsEPNbKlh_YRApruSi03WMTofKSq1yYT2w_pT9CCJvL6YQ9VqHrKHKEHtrhLy2y6jB16ohvx1F2E9ZhCemuicD7oaMMY0iJY9h0bbNeZpEA-yasUwaI1FKEfozwQ9aFdsAB2wYziGEF_bjcDYsYEKIf_Wf2sYY20Zd_84D9Pj_7VX3n86vZj-pkztFMVcm9xVwLVAtbm9xMF7X1WnokRdYX1ntEK7UsyExLMB5lXUBemtGjJKPI6wN2uMvtYnjYUOrdqknjpS2sKWySk4WQosjL0v6nLz9Gql0XmxXEwUnhtt26sVu37XakfEcfm5aGd507uare-ib19PTqId67vNCFcbc_Z-5SX89O5-Wtu9DPa9eMUg</recordid><startdate>201506</startdate><enddate>201506</enddate><creator>Xu, Wei</creator><creator>Yu, Bo</creator><creator>Sun, Huaming</creator><creator>Zhang, Guofang</creator><creator>Zhang, Weiqiang</creator><creator>Gao, Ziwei</creator><general>Blackwell Publishing Ltd</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>FR3</scope><scope>JG9</scope><scope>KR7</scope><scope>L7M</scope></search><sort><creationdate>201506</creationdate><title>Copper-catalyzed C(sp2)-C(sp) Sonogashira-type cross-coupling reactions accelerated by polycyclic aromatic hydrocarbons</title><author>Xu, Wei ; Yu, Bo ; Sun, Huaming ; Zhang, Guofang ; Zhang, Weiqiang ; Gao, Ziwei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5428-b9c630c2d9f5654df9b31bce2e9b79bbcc91317e548a5bc1f7a685c2dc1e52eb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chemical compounds</topic><topic>Copper</topic><topic>copper catalysis</topic><topic>Iodides</topic><topic>Polycyclic aromatic hydrocarbons</topic><topic>Pyrenes</topic><topic>Sonogashira-type cross-coupling reaction</topic><topic>Terminals</topic><topic>Tolerances</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Xu, Wei</creatorcontrib><creatorcontrib>Yu, Bo</creatorcontrib><creatorcontrib>Sun, Huaming</creatorcontrib><creatorcontrib>Zhang, Guofang</creatorcontrib><creatorcontrib>Zhang, Weiqiang</creatorcontrib><creatorcontrib>Gao, Ziwei</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Materials Research Database</collection><collection>Civil Engineering Abstracts</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Applied organometallic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Xu, Wei</au><au>Yu, Bo</au><au>Sun, Huaming</au><au>Zhang, Guofang</au><au>Zhang, Weiqiang</au><au>Gao, Ziwei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper-catalyzed C(sp2)-C(sp) Sonogashira-type cross-coupling reactions accelerated by polycyclic aromatic hydrocarbons</atitle><jtitle>Applied organometallic chemistry</jtitle><addtitle>Appl. Organometal. Chem</addtitle><date>2015-06</date><risdate>2015</risdate><volume>29</volume><issue>6</issue><spage>353</spage><epage>356</epage><pages>353-356</pages><issn>0268-2605</issn><eissn>1099-0739</eissn><abstract>Copper‐catalyzed Sonogashira‐type reactions were dramatically accelerated by introducing a catalytic amount of polycyclic aromatic hydrocarbon additive. This novel catalytic system features low copper loading (0.5 mol% < Cu < 5 mol%), broad reaction scope and remarkable substrate tolerance. Both aromatic and aliphatic terminal alkynes as well as diverse aryl iodides were employed in this transformation, affording respectable yields of the desired products. The novel Cu(OTf)2/pyrene system was subsequently employed to synthesize phenylacetylene‐based fluorescent compounds. Copyright © 2015 John Wiley & Sons, Ltd.
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| source | Wiley Online Library Journals |
| subjects | Catalysis Catalysts Chemical compounds Copper copper catalysis Iodides Polycyclic aromatic hydrocarbons Pyrenes Sonogashira-type cross-coupling reaction Terminals Tolerances |
| title | Copper-catalyzed C(sp2)-C(sp) Sonogashira-type cross-coupling reactions accelerated by polycyclic aromatic hydrocarbons |
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