Stereoselective Suzuki−Miyaura Cross-Coupling Reactions of Potassium Alkenyltrifluoroborates with Alkenyl Bromides
The stereoselective synthesis of conjugated dienes using air-stable potassium alkenyltrifluoroborates as coupling partners is described. The palladium-catalyzed cross-coupling reaction of potassium (E)- and (Z)-alkenyltrifluoroborates with either (E)- or (Z)-alkenyl bromides proceeds readily with mo...
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| Veröffentlicht in: | Journal of organic chemistry 2005-05, Vol.70 (10), p.3950-3956 |
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| container_title | Journal of organic chemistry |
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| creator | Molander, Gary A Felix, Luciana A |
| description | The stereoselective synthesis of conjugated dienes using air-stable potassium alkenyltrifluoroborates as coupling partners is described. The palladium-catalyzed cross-coupling reaction of potassium (E)- and (Z)-alkenyltrifluoroborates with either (E)- or (Z)-alkenyl bromides proceeds readily with moderate to excellent yields to give the corresponding (E,E)-, (E,Z)-, (Z,E)-, or (Z,Z)-conjugated dienes stereospecifically. The cross-coupling can generally be effected using 5 mol % of Pd(OAc)2, 10 mol % of PPh3, and 3 equiv of Cs2CO3 in THF−H2O (10:1). A variety of functional groups are tolerated in both coupling partners. |
| doi_str_mv | 10.1021/jo050286w |
| format | Article |
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The palladium-catalyzed cross-coupling reaction of potassium (E)- and (Z)-alkenyltrifluoroborates with either (E)- or (Z)-alkenyl bromides proceeds readily with moderate to excellent yields to give the corresponding (E,E)-, (E,Z)-, (Z,E)-, or (Z,Z)-conjugated dienes stereospecifically. The cross-coupling can generally be effected using 5 mol % of Pd(OAc)2, 10 mol % of PPh3, and 3 equiv of Cs2CO3 in THF−H2O (10:1). A variety of functional groups are tolerated in both coupling partners.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo050286w</identifier><identifier>PMID: 15876083</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Aliphatic compounds ; Alkenes - chemical synthesis ; Alkenes - chemistry ; Borates - chemistry ; Bromine - chemistry ; Catalysis ; Chemistry ; Exact sciences and technology ; Organic chemistry ; Preparations and properties ; Stereoisomerism</subject><ispartof>Journal of organic chemistry, 2005-05, Vol.70 (10), p.3950-3956</ispartof><rights>Copyright © 2005 American Chemical Society</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-cca0c7e61a99d7c777b375901ed99589678bea955202b0ac3eb35c4a5520a6e83</citedby><cites>FETCH-LOGICAL-a381t-cca0c7e61a99d7c777b375901ed99589678bea955202b0ac3eb35c4a5520a6e83</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo050286w$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo050286w$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=16780435$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15876083$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Molander, Gary A</creatorcontrib><creatorcontrib>Felix, Luciana A</creatorcontrib><title>Stereoselective Suzuki−Miyaura Cross-Coupling Reactions of Potassium Alkenyltrifluoroborates with Alkenyl Bromides</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The stereoselective synthesis of conjugated dienes using air-stable potassium alkenyltrifluoroborates as coupling partners is described. The palladium-catalyzed cross-coupling reaction of potassium (E)- and (Z)-alkenyltrifluoroborates with either (E)- or (Z)-alkenyl bromides proceeds readily with moderate to excellent yields to give the corresponding (E,E)-, (E,Z)-, (Z,E)-, or (Z,Z)-conjugated dienes stereospecifically. The cross-coupling can generally be effected using 5 mol % of Pd(OAc)2, 10 mol % of PPh3, and 3 equiv of Cs2CO3 in THF−H2O (10:1). A variety of functional groups are tolerated in both coupling partners.</description><subject>Aliphatic compounds</subject><subject>Alkenes - chemical synthesis</subject><subject>Alkenes - chemistry</subject><subject>Borates - chemistry</subject><subject>Bromine - chemistry</subject><subject>Catalysis</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkM1uEzEUhS1ERUNhwQug2YDUxYA9judnWSIKiACFFNSddce5A2484-AfSvoEXfcReRI8Smg2eHMl30_nnnMIecLoC0YL9vLSUkGLury6RyZMFDQvGzq9TyaUFkXOi5IfkofeX9L0hBAPyCETdVXSmk9IWAR0aD0aVEH_wmwRr-NK_7m5_aA3EB1kM2e9z2c2ro0evmdfEBJoB5_ZLjuzAbzXsc9OzAqHjQlOdyZaZ1vrIKDPrnT48W-ZvXK210v0j8hBB8bj4908Il9PX5_P3ubzT2_ezU7mOfCahVwpoKrCkkHTLCtVVVXLK9FQhsumEXVTVnWL0IiUuGgpKI4tF2oK4weUWPMj8nyru3b2Z0QfZK-9QmNgQBu9TAK0YlQk8HgLqjGsw06une7BbSSjcqxY3lWc2Kc70dj2uNyTu04T8GwHgFdgOgeD0n7PjVenfDyabzntA_6-24NbJWMpqDw_W8j3c3rxWVx8lN_2uqB88hPdkLr7j8G_Z0Cikg</recordid><startdate>20050513</startdate><enddate>20050513</enddate><creator>Molander, Gary A</creator><creator>Felix, Luciana A</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</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>7X8</scope></search><sort><creationdate>20050513</creationdate><title>Stereoselective Suzuki−Miyaura Cross-Coupling Reactions of Potassium Alkenyltrifluoroborates with Alkenyl Bromides</title><author>Molander, Gary A ; Felix, Luciana A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-cca0c7e61a99d7c777b375901ed99589678bea955202b0ac3eb35c4a5520a6e83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Aliphatic compounds</topic><topic>Alkenes - chemical synthesis</topic><topic>Alkenes - chemistry</topic><topic>Borates - chemistry</topic><topic>Bromine - chemistry</topic><topic>Catalysis</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Molander, Gary A</creatorcontrib><creatorcontrib>Felix, Luciana A</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><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><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Molander, Gary A</au><au>Felix, Luciana A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Stereoselective Suzuki−Miyaura Cross-Coupling Reactions of Potassium Alkenyltrifluoroborates with Alkenyl Bromides</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2005-05-13</date><risdate>2005</risdate><volume>70</volume><issue>10</issue><spage>3950</spage><epage>3956</epage><pages>3950-3956</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The stereoselective synthesis of conjugated dienes using air-stable potassium alkenyltrifluoroborates as coupling partners is described. The palladium-catalyzed cross-coupling reaction of potassium (E)- and (Z)-alkenyltrifluoroborates with either (E)- or (Z)-alkenyl bromides proceeds readily with moderate to excellent yields to give the corresponding (E,E)-, (E,Z)-, (Z,E)-, or (Z,Z)-conjugated dienes stereospecifically. The cross-coupling can generally be effected using 5 mol % of Pd(OAc)2, 10 mol % of PPh3, and 3 equiv of Cs2CO3 in THF−H2O (10:1). A variety of functional groups are tolerated in both coupling partners.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15876083</pmid><doi>10.1021/jo050286w</doi><tpages>7</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 2005-05, Vol.70 (10), p.3950-3956 |
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| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Aliphatic compounds Alkenes - chemical synthesis Alkenes - chemistry Borates - chemistry Bromine - chemistry Catalysis Chemistry Exact sciences and technology Organic chemistry Preparations and properties Stereoisomerism |
| title | Stereoselective Suzuki−Miyaura Cross-Coupling Reactions of Potassium Alkenyltrifluoroborates with Alkenyl Bromides |
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