Synthesis of Substituted Naphthalenes and Carbazoles by the Palladium-Catalyzed Annulation of Internal Alkynes
An efficient synthesis of highly substituted naphthalenes has been developed by the palladium-catalyzed annulation of a variety of internal alkynes, in which two new carbon−carbon bonds are formed in a single step under relatively mild reaction conditions. This method has also been used to synthesiz...
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| Veröffentlicht in: | Journal of organic chemistry 2003-09, Vol.68 (19), p.7342-7349 |
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| container_end_page | 7349 |
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| container_title | Journal of organic chemistry |
| container_volume | 68 |
| creator | Huang, Qinhua Larock, Richard C |
| description | An efficient synthesis of highly substituted naphthalenes has been developed by the palladium-catalyzed annulation of a variety of internal alkynes, in which two new carbon−carbon bonds are formed in a single step under relatively mild reaction conditions. This method has also been used to synthesize carbazoles, although a higher reaction temperature is necessary. The process involves arylpalladation of the alkyne, followed by intramolecular Heck olefination and double-bond isomerization. This method accommodates a variety of functional groups and affords the anticipated highly substituted naphthalenes and carbazoles in good to excellent yields. |
| doi_str_mv | 10.1021/jo034449x |
| format | Article |
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This method has also been used to synthesize carbazoles, although a higher reaction temperature is necessary. The process involves arylpalladation of the alkyne, followed by intramolecular Heck olefination and double-bond isomerization. This method accommodates a variety of functional groups and affords the anticipated highly substituted naphthalenes and carbazoles in good to excellent yields.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo034449x</identifier><identifier>PMID: 12968885</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 ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Organic chemistry ; Preparations and properties</subject><ispartof>Journal of organic chemistry, 2003-09, Vol.68 (19), p.7342-7349</ispartof><rights>Copyright © 2003 American Chemical Society</rights><rights>2004 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a445t-c014bc344c8797ef9fd6e281b6e883abe56c83698ba94f9213e39aed6014b56c3</citedby><cites>FETCH-LOGICAL-a445t-c014bc344c8797ef9fd6e281b6e883abe56c83698ba94f9213e39aed6014b56c3</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/jo034449x$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo034449x$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,777,781,2752,27057,27905,27906,56719,56769</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15121829$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/12968885$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Huang, Qinhua</creatorcontrib><creatorcontrib>Larock, Richard C</creatorcontrib><title>Synthesis of Substituted Naphthalenes and Carbazoles by the Palladium-Catalyzed Annulation of Internal Alkynes</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>An efficient synthesis of highly substituted naphthalenes has been developed by the palladium-catalyzed annulation of a variety of internal alkynes, in which two new carbon−carbon bonds are formed in a single step under relatively mild reaction conditions. This method has also been used to synthesize carbazoles, although a higher reaction temperature is necessary. The process involves arylpalladation of the alkyne, followed by intramolecular Heck olefination and double-bond isomerization. This method accommodates a variety of functional groups and affords the anticipated highly substituted naphthalenes and carbazoles in good to excellent yields.</description><subject>Chemistry</subject><subject>Condensed benzenic and aromatic compounds</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</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>2003</creationdate><recordtype>article</recordtype><recordid>eNptkEtrGzEUhUVpSJw0i_6BMpsWuphUj5FGWhqneUDaGpyuxR2NBk8ia1xJA5n8-srYxJvcjbjc7xyODkKfCb4imJIfTwNmVVWplw9oRjjFpVC4-ohmGFNaMirYGTqP8Qnn4ZyfojNClZBS8hnyq8mntY19LIauWI1NTH0ak22L37BdpzU4620swLfFAkIDr4PLazMVWVQswTlo-3FTLiCBm16zbO796CD1g98Z3vtkgwdXzN3zlI0-oZMOXLSXh_cC_b35-bi4Kx_-3N4v5g8lVBVPpcGkakz-k5G1qm2nulZYKkkjrJQMGsuFkUwo2YCqOkUJs0yBbcVOl2_sAn3b-27D8G-0MelNH43Ncb0dxqhrJhitJM3g9z1owhBjsJ3ehn4DYdIE6125-q3czH45mI7NxrZH8tBmBr4eAIgGXBfAmz4eOU4okVRlrtxzfUz25e0O4VmLmtVcPy5Xmt_e1fjm-pdeHn3BxJxn3DUa3wn4H56Znhg</recordid><startdate>20030919</startdate><enddate>20030919</enddate><creator>Huang, Qinhua</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>20030919</creationdate><title>Synthesis of Substituted Naphthalenes and Carbazoles by the Palladium-Catalyzed Annulation of Internal Alkynes</title><author>Huang, Qinhua ; Larock, Richard C</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a445t-c014bc344c8797ef9fd6e281b6e883abe56c83698ba94f9213e39aed6014b56c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2003</creationdate><topic>Chemistry</topic><topic>Condensed benzenic and aromatic compounds</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Huang, Qinhua</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>Huang, Qinhua</au><au>Larock, Richard C</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Substituted Naphthalenes and Carbazoles by the Palladium-Catalyzed Annulation of Internal Alkynes</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2003-09-19</date><risdate>2003</risdate><volume>68</volume><issue>19</issue><spage>7342</spage><epage>7349</epage><pages>7342-7349</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>An efficient synthesis of highly substituted naphthalenes has been developed by the palladium-catalyzed annulation of a variety of internal alkynes, in which two new carbon−carbon bonds are formed in a single step under relatively mild reaction conditions. This method has also been used to synthesize carbazoles, although a higher reaction temperature is necessary. The process involves arylpalladation of the alkyne, followed by intramolecular Heck olefination and double-bond isomerization. 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| source | ACS Publications |
| subjects | Chemistry Condensed benzenic and aromatic compounds Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Preparations and properties |
| title | Synthesis of Substituted Naphthalenes and Carbazoles by the Palladium-Catalyzed Annulation of Internal Alkynes |
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