Multimetallic Ni- and Pd-Catalyzed Cross-Electrophile Coupling To Form Highly Substituted 1,3-Dienes

The synthesis of highly substituted 1,3-dienes from the coupling of vinyl bromides with vinyl triflates is reported for the first time. The coupling is catalyzed by a combination of (5,5′-bis(trifluoromethyl)-2,2′-bipyridine)NiBr2 and (1,3-bis(diphenylphosphino)propane)PdCl2 in the presence of...

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Veröffentlicht in:	Journal of the American Chemical Society 2018-02, Vol.140 (7), p.2446-2449
Hauptverfasser:	Olivares, Astrid M, Weix, Daniel J
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkadienes - chemical synthesis Alkadienes - chemistry Catalysis Molecular Structure Nickel - chemistry Organometallic Compounds - chemistry Palladium - chemistry
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container_title	Journal of the American Chemical Society
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creator	Olivares, Astrid M Weix, Daniel J
description	The synthesis of highly substituted 1,3-dienes from the coupling of vinyl bromides with vinyl triflates is reported for the first time. The coupling is catalyzed by a combination of (5,5′-bis(trifluoromethyl)-2,2′-bipyridine)NiBr2 and (1,3-bis(diphenylphosphino)propane)PdCl2 in the presence of a zinc reductant. This method affords tetra- and penta-substituted 1,3-dienes that would otherwise be difficult to access and tolerates electron-rich and -poor substituents, heterocycles, an aryl bromide, and a pinacol boronate ester. Mechanistically, the reaction appears to proceed by an unusual zinc-mediated transfer of a vinyl group between the nickel and palladium centers.
doi_str_mv	10.1021/jacs.7b13601
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Mechanistically, the reaction appears to proceed by an unusual zinc-mediated transfer of a vinyl group between the nickel and palladium centers.</description><subject>Alkadienes - chemical synthesis</subject><subject>Alkadienes - chemistry</subject><subject>Catalysis</subject><subject>Molecular Structure</subject><subject>Nickel - chemistry</subject><subject>Organometallic Compounds - chemistry</subject><subject>Palladium - chemistry</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptUU1v1DAQtRCIbgs3zshHDnWxndjJXpBQ6AdSW5DYu-XYk12vnHixHaTl1-NVl9JKnEYz8-bNzHsIvWP0glHOPm61SRdNzypJ2Qu0YIJTIhiXL9GCUspJ08rqBJ2mtC1pzVv2Gp3wZc1Lr10gezf77EbI2ntn8L0jWE8Wf7ek06W2_w0WdzGkRC49mBzDbuM84C7MO--mNV4FfBXiiG_ceuP3-Mfcp-zynMsYO6_IFwcTpDfo1aB9grfHeIZWV5er7obcfrv-2n2-JbocnYnWjMl62fbUyLp8YyoYGk77emiZMZYtG0mFGJqhByn0Uoq-FRQ0WGENt311hj490O7mfgRrYMpRe7WLbtRxr4J26nlnchu1Dr-UaHmRrSoEH44EMfycIWU1umTAez1BmJMqmjEqZV2xAj1_gJqDOBGGxzWMqoMv6uCLOvpS4O-fnvYI_mvEv9WHqW2Y41SE-j_XH2nNl3M</recordid><startdate>20180221</startdate><enddate>20180221</enddate><creator>Olivares, Astrid M</creator><creator>Weix, Daniel J</creator><general>American Chemical Society</general><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>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-9552-3378</orcidid></search><sort><creationdate>20180221</creationdate><title>Multimetallic Ni- and Pd-Catalyzed Cross-Electrophile Coupling To Form Highly Substituted 1,3-Dienes</title><author>Olivares, Astrid M ; Weix, Daniel J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a520t-aa116498b0c64601c3ef720b4f81ccd1976055f7fbe65a965b850eaed5dc2db3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Alkadienes - chemical synthesis</topic><topic>Alkadienes - chemistry</topic><topic>Catalysis</topic><topic>Molecular Structure</topic><topic>Nickel - chemistry</topic><topic>Organometallic Compounds - chemistry</topic><topic>Palladium - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Olivares, Astrid M</creatorcontrib><creatorcontrib>Weix, Daniel J</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Olivares, Astrid M</au><au>Weix, Daniel J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Multimetallic Ni- and Pd-Catalyzed Cross-Electrophile Coupling To Form Highly Substituted 1,3-Dienes</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2018-02-21</date><risdate>2018</risdate><volume>140</volume><issue>7</issue><spage>2446</spage><epage>2449</epage><pages>2446-2449</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>The synthesis of highly substituted 1,3-dienes from the coupling of vinyl bromides with vinyl triflates is reported for the first time. The coupling is catalyzed by a combination of (5,5′-bis(trifluoromethyl)-2,2′-bipyridine)NiBr2 and (1,3-bis(diphenylphosphino)propane)PdCl2 in the presence of a zinc reductant. This method affords tetra- and penta-substituted 1,3-dienes that would otherwise be difficult to access and tolerates electron-rich and -poor substituents, heterocycles, an aryl bromide, and a pinacol boronate ester. 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subjects	Alkadienes - chemical synthesis Alkadienes - chemistry Catalysis Molecular Structure Nickel - chemistry Organometallic Compounds - chemistry Palladium - chemistry
title	Multimetallic Ni- and Pd-Catalyzed Cross-Electrophile Coupling To Form Highly Substituted 1,3-Dienes
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