Rh-Catalyzed Oxidative Coupling between Primary and Secondary Benzamides and Alkynes: Synthesis of Polycyclic Amides
A methodology for the high yield and facile synthesis of isoquinolones from benzamides and alkynes via the oxidative ortho C−H activation of benzamides has been developed. Ag2CO3 proved to be an optimal oxidant when MeCN was used as a solvent, and [RhCp*Cl2]2 was utilized as an efficient catalyst. B...
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| Veröffentlicht in: | Journal of organic chemistry 2010-11, Vol.75 (21), p.7487-7490 |
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| container_end_page | 7490 |
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| container_issue | 21 |
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| container_title | Journal of organic chemistry |
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| creator | Song, Guoyong Chen, Dan Pan, Cheng-Ling Crabtree, Robert H Li, Xingwei |
| description | A methodology for the high yield and facile synthesis of isoquinolones from benzamides and alkynes via the oxidative ortho C−H activation of benzamides has been developed. Ag2CO3 proved to be an optimal oxidant when MeCN was used as a solvent, and [RhCp*Cl2]2 was utilized as an efficient catalyst. Both N-alkyl and N-aryl secondary benzamides can be applied as effective substrates. Furthermore, primary benzamides react with two alkyne units, leading to tricyclic products via double C−H activation and oxidative coupling. The reactivity of the structurally related 1-hydroxyisoquinoline was also demonstrated, where both N- and O-containing rhodacyclic intermediates can be generated, leading to the construction of different O- or N-containing heterocycles. |
| doi_str_mv | 10.1021/jo101596d |
| format | Article |
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Ag2CO3 proved to be an optimal oxidant when MeCN was used as a solvent, and [RhCp*Cl2]2 was utilized as an efficient catalyst. Both N-alkyl and N-aryl secondary benzamides can be applied as effective substrates. Furthermore, primary benzamides react with two alkyne units, leading to tricyclic products via double C−H activation and oxidative coupling. The reactivity of the structurally related 1-hydroxyisoquinoline was also demonstrated, where both N- and O-containing rhodacyclic intermediates can be generated, leading to the construction of different O- or N-containing heterocycles.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo101596d</identifier><identifier>PMID: 20923219</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Alkynes - chemistry ; Benzamides - chemistry ; Catalysis ; Catalysts: preparations and properties ; Chemical reactivity ; Chemistry ; Exact sciences and technology ; General and physical chemistry ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Organic chemistry ; Oxidation-Reduction ; Polycyclic Compounds - chemistry ; Preparations and properties ; Reactivity and mechanisms ; Rhodium - chemistry ; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><ispartof>Journal of organic chemistry, 2010-11, Vol.75 (21), p.7487-7490</ispartof><rights>Copyright © 2010 American Chemical Society</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a410t-722b9708f947be4ca0fa1751b2b1263734c2a6ae0235d7b27a00deacf7905b843</citedby><cites>FETCH-LOGICAL-a410t-722b9708f947be4ca0fa1751b2b1263734c2a6ae0235d7b27a00deacf7905b843</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/jo101596d$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo101596d$$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=23386847$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20923219$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Song, Guoyong</creatorcontrib><creatorcontrib>Chen, Dan</creatorcontrib><creatorcontrib>Pan, Cheng-Ling</creatorcontrib><creatorcontrib>Crabtree, Robert H</creatorcontrib><creatorcontrib>Li, Xingwei</creatorcontrib><title>Rh-Catalyzed Oxidative Coupling between Primary and Secondary Benzamides and Alkynes: Synthesis of Polycyclic Amides</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>A methodology for the high yield and facile synthesis of isoquinolones from benzamides and alkynes via the oxidative ortho C−H activation of benzamides has been developed. Ag2CO3 proved to be an optimal oxidant when MeCN was used as a solvent, and [RhCp*Cl2]2 was utilized as an efficient catalyst. Both N-alkyl and N-aryl secondary benzamides can be applied as effective substrates. Furthermore, primary benzamides react with two alkyne units, leading to tricyclic products via double C−H activation and oxidative coupling. The reactivity of the structurally related 1-hydroxyisoquinoline was also demonstrated, where both N- and O-containing rhodacyclic intermediates can be generated, leading to the construction of different O- or N-containing heterocycles.</description><subject>Alkynes - chemistry</subject><subject>Benzamides - chemistry</subject><subject>Catalysis</subject><subject>Catalysts: preparations and properties</subject><subject>Chemical reactivity</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>General and physical chemistry</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Organic chemistry</subject><subject>Oxidation-Reduction</subject><subject>Polycyclic Compounds - chemistry</subject><subject>Preparations and properties</subject><subject>Reactivity and mechanisms</subject><subject>Rhodium - chemistry</subject><subject>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0E1P3DAQBmCrKioL7aF_oPKlqjgExk4cb3rbrviSkFiV9hxN7Ekx9TpLnADh1xN2F7jgi2XNo9eal7GvAg4FSHF00wgQqsjtBzYRSkKSF5B9ZBMAKZNU5uku24vxBsajlPrEdiUUMpWimLDu93Uyxw798EiWXz44i527Iz5v-pV34R-vqLsnCnzRuiW2A8dg-RWZJtjn1y8Kj7h0luJ6MPP_h0DxJ78aQndN0UXe1HzR-MEMxjvDZ2v7me3U6CN92d777O_J8Z_5WXJxeXo-n10kmAnoEi1lVWiY1kWmK8oMQo1CK1HJSoxL6TQzEnMkkKmyupIaASyhqXUBqppm6T77scldtc1tT7Erly4a8h4DNX0sdS4zrQuVj_JgI03bxNhSXa42-5YCyueOy9eOR_ttm9pXS7Kv8qXUEXzfAowGfd1iMC6-uTSd5tNMvzk0cczv2zCW8c6HTy6xkFI</recordid><startdate>20101105</startdate><enddate>20101105</enddate><creator>Song, Guoyong</creator><creator>Chen, Dan</creator><creator>Pan, Cheng-Ling</creator><creator>Crabtree, Robert H</creator><creator>Li, Xingwei</creator><general>American Chemical Society</general><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>20101105</creationdate><title>Rh-Catalyzed Oxidative Coupling between Primary and Secondary Benzamides and Alkynes: Synthesis of Polycyclic Amides</title><author>Song, Guoyong ; Chen, Dan ; Pan, Cheng-Ling ; Crabtree, Robert H ; Li, Xingwei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a410t-722b9708f947be4ca0fa1751b2b1263734c2a6ae0235d7b27a00deacf7905b843</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Alkynes - chemistry</topic><topic>Benzamides - chemistry</topic><topic>Catalysis</topic><topic>Catalysts: preparations and properties</topic><topic>Chemical reactivity</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>General and physical chemistry</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Organic chemistry</topic><topic>Oxidation-Reduction</topic><topic>Polycyclic Compounds - chemistry</topic><topic>Preparations and properties</topic><topic>Reactivity and mechanisms</topic><topic>Rhodium - chemistry</topic><topic>Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Song, Guoyong</creatorcontrib><creatorcontrib>Chen, Dan</creatorcontrib><creatorcontrib>Pan, Cheng-Ling</creatorcontrib><creatorcontrib>Crabtree, Robert H</creatorcontrib><creatorcontrib>Li, Xingwei</creatorcontrib><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>Song, Guoyong</au><au>Chen, Dan</au><au>Pan, Cheng-Ling</au><au>Crabtree, Robert H</au><au>Li, Xingwei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Rh-Catalyzed Oxidative Coupling between Primary and Secondary Benzamides and Alkynes: Synthesis of Polycyclic Amides</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2010-11-05</date><risdate>2010</risdate><volume>75</volume><issue>21</issue><spage>7487</spage><epage>7490</epage><pages>7487-7490</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>A methodology for the high yield and facile synthesis of isoquinolones from benzamides and alkynes via the oxidative ortho C−H activation of benzamides has been developed. Ag2CO3 proved to be an optimal oxidant when MeCN was used as a solvent, and [RhCp*Cl2]2 was utilized as an efficient catalyst. Both N-alkyl and N-aryl secondary benzamides can be applied as effective substrates. Furthermore, primary benzamides react with two alkyne units, leading to tricyclic products via double C−H activation and oxidative coupling. The reactivity of the structurally related 1-hydroxyisoquinoline was also demonstrated, where both N- and O-containing rhodacyclic intermediates can be generated, leading to the construction of different O- or N-containing heterocycles.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>20923219</pmid><doi>10.1021/jo101596d</doi><tpages>4</tpages></addata></record> |
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| subjects | Alkynes - chemistry Benzamides - chemistry Catalysis Catalysts: preparations and properties Chemical reactivity Chemistry Exact sciences and technology General and physical chemistry Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Oxidation-Reduction Polycyclic Compounds - chemistry Preparations and properties Reactivity and mechanisms Rhodium - chemistry Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry |
| title | Rh-Catalyzed Oxidative Coupling between Primary and Secondary Benzamides and Alkynes: Synthesis of Polycyclic Amides |
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