Carbopalladation of Nitriles: Synthesis of 2,3-Diarylindenones and Polycyclic Aromatic Ketones by the Pd-Catalyzed Annulation of Alkynes and Bicyclic Alkenes by 2-Iodoarenenitriles
2-Iodobenzonitrile, its derivatives, and various heterocyclic analogues undergo palladium(0)-catalyzed annulation onto diarylacetylenes or bicyclic alkenes to afford 2,3-diarylindenones and polycyclic aromatic ketones in very good to excellent yields. This reaction represents one of the first exampl...
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| Veröffentlicht in: | Journal of organic chemistry 2002-12, Vol.67 (26), p.9276-9287 |
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| container_end_page | 9287 |
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| container_issue | 26 |
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| container_title | Journal of organic chemistry |
| container_volume | 67 |
| creator | Pletnev, Alexandre A Tian, Qingping Larock, Richard C |
| description | 2-Iodobenzonitrile, its derivatives, and various heterocyclic analogues undergo palladium(0)-catalyzed annulation onto diarylacetylenes or bicyclic alkenes to afford 2,3-diarylindenones and polycyclic aromatic ketones in very good to excellent yields. This reaction represents one of the first examples of the addition of an organopalladium moiety to the carbon−nitrogen triple bond of a nitrile. The reaction is compatible with a number of functional groups. A reaction mechanism, as well as a model accounting for the electronic effects of substituents on the aromatic ring of the nitrile, is proposed. |
| doi_str_mv | 10.1021/jo026178g |
| format | Article |
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This reaction represents one of the first examples of the addition of an organopalladium moiety to the carbon−nitrogen triple bond of a nitrile. The reaction is compatible with a number of functional groups. A reaction mechanism, as well as a model accounting for the electronic effects of substituents on the aromatic ring of the nitrile, is proposed.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo026178g</identifier><identifier>PMID: 12492329</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Chemistry ; Condensed benzenic and aromatic compounds ; Exact sciences and technology ; Organic chemistry ; Preparations and properties</subject><ispartof>Journal of organic chemistry, 2002-12, Vol.67 (26), p.9276-9287</ispartof><rights>Copyright © 2002 American Chemical Society</rights><rights>2003 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a445t-17125aecf8e88dffc1706a53368f1fe48c8e8f6ea6c1debb6669eace6d7ac2853</citedby><cites>FETCH-LOGICAL-a445t-17125aecf8e88dffc1706a53368f1fe48c8e8f6ea6c1debb6669eace6d7ac2853</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/jo026178g$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo026178g$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,782,786,2767,27083,27931,27932,56745,56795</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=14447978$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12492329$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Pletnev, Alexandre A</creatorcontrib><creatorcontrib>Tian, Qingping</creatorcontrib><creatorcontrib>Larock, Richard C</creatorcontrib><title>Carbopalladation of Nitriles: Synthesis of 2,3-Diarylindenones and Polycyclic Aromatic Ketones by the Pd-Catalyzed Annulation of Alkynes and Bicyclic Alkenes by 2-Iodoarenenitriles</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>2-Iodobenzonitrile, its derivatives, and various heterocyclic analogues undergo palladium(0)-catalyzed annulation onto diarylacetylenes or bicyclic alkenes to afford 2,3-diarylindenones and polycyclic aromatic ketones in very good to excellent yields. This reaction represents one of the first examples of the addition of an organopalladium moiety to the carbon−nitrogen triple bond of a nitrile. The reaction is compatible with a number of functional groups. A reaction mechanism, as well as a model accounting for the electronic effects of substituents on the aromatic ring of the nitrile, is proposed.</description><subject>Chemistry</subject><subject>Condensed benzenic and aromatic compounds</subject><subject>Exact sciences and technology</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><recordid>eNptkc-O0zAQhyMEYrsLB14A5QISEgHbSRxnb6XLn9WuoNAiJC7R1BmDt65d7EQinLjyRLwPT4KXZtsLvljW7_M3o5kkeUDJM0oYfX7lCOO0El9uJRNaMpLxmhS3kwkhjGU54_lRchzCFYmnLMu7yRFlRc1yVk-S3zPwK7cFY6CFTjubOpW-1Z3XBsPpn5-_0sVgu68YdLhO2NM8O9PgB6Nti9ZZDCnYNp07M8hBGi3TqXebaJLpBXb_8tWQRkE6b7MZdGCGH9imU2t7s683NevhxvRC33jMGsfvLDt3rQMf33Zs7V5yR4EJeH-8T5KPr14uZ2-yy3evz2fTywyKouwyWlFWAkolUIhWKUkrwqHMcy4UVVgIGQPFEbikLa5WnPMaQSJvK5BMlPlJ8njn3Xr3rcfQNRsdJMZxWXR9aCpWCUHqOoJPdqD0LgSPqtl6vYmTaihprrfU7LcU2YejtF9tsD2Q41oi8GgEIEgwyoOVOhy4oiiquhKRy3acDh1-3-fg1w2v8qpslvNFc7H8JN6zzx-axcELMsR-em_j7P7T4F-BBLob</recordid><startdate>20021227</startdate><enddate>20021227</enddate><creator>Pletnev, Alexandre A</creator><creator>Tian, Qingping</creator><creator>Larock, Richard C</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20021227</creationdate><title>Carbopalladation of Nitriles: Synthesis of 2,3-Diarylindenones and Polycyclic Aromatic Ketones by the Pd-Catalyzed Annulation of Alkynes and Bicyclic Alkenes by 2-Iodoarenenitriles</title><author>Pletnev, Alexandre A ; Tian, Qingping ; Larock, Richard C</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a445t-17125aecf8e88dffc1706a53368f1fe48c8e8f6ea6c1debb6669eace6d7ac2853</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2002</creationdate><topic>Chemistry</topic><topic>Condensed benzenic and aromatic compounds</topic><topic>Exact sciences and technology</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pletnev, Alexandre A</creatorcontrib><creatorcontrib>Tian, Qingping</creatorcontrib><creatorcontrib>Larock, Richard C</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</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>Pletnev, Alexandre A</au><au>Tian, Qingping</au><au>Larock, Richard C</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Carbopalladation of Nitriles: Synthesis of 2,3-Diarylindenones and Polycyclic Aromatic Ketones by the Pd-Catalyzed Annulation of Alkynes and Bicyclic Alkenes by 2-Iodoarenenitriles</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2002-12-27</date><risdate>2002</risdate><volume>67</volume><issue>26</issue><spage>9276</spage><epage>9287</epage><pages>9276-9287</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>2-Iodobenzonitrile, its derivatives, and various heterocyclic analogues undergo palladium(0)-catalyzed annulation onto diarylacetylenes or bicyclic alkenes to afford 2,3-diarylindenones and polycyclic aromatic ketones in very good to excellent yields. This reaction represents one of the first examples of the addition of an organopalladium moiety to the carbon−nitrogen triple bond of a nitrile. The reaction is compatible with a number of functional groups. A reaction mechanism, as well as a model accounting for the electronic effects of substituents on the aromatic ring of the nitrile, is proposed.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12492329</pmid><doi>10.1021/jo026178g</doi><tpages>12</tpages></addata></record> |
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| ispartof | Journal of organic chemistry, 2002-12, Vol.67 (26), p.9276-9287 |
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| language | eng |
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| source | ACS Publications |
| subjects | Chemistry Condensed benzenic and aromatic compounds Exact sciences and technology Organic chemistry Preparations and properties |
| title | Carbopalladation of Nitriles: Synthesis of 2,3-Diarylindenones and Polycyclic Aromatic Ketones by the Pd-Catalyzed Annulation of Alkynes and Bicyclic Alkenes by 2-Iodoarenenitriles |
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