Cu(II)‐Mediated C−C/C−O Bond Formation via C−H/C−C Bond Cleavage: Access to Benzofurans Using Amide as a Traceless Directing Group
A copper‐mediated synthesis of 2,3‐disubstituted benzofurans with the assistance of an 8‐aminoquinolyl auxiliary is described from readily available benzamides and benzoylacetonitriles. In this reaction, the C−C bond is successfully constructed via C−H activation, and C−O bond is subsequently formed...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2020-01, Vol.362 (1), p.118-125 |
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| container_end_page | 125 |
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| container_issue | 1 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Yu, Shuling Lv, Ningning Liu, Zhanxiang Zhang, Yuhong |
| description | A copper‐mediated synthesis of 2,3‐disubstituted benzofurans with the assistance of an 8‐aminoquinolyl auxiliary is described from readily available benzamides and benzoylacetonitriles. In this reaction, the C−C bond is successfully constructed via C−H activation, and C−O bond is subsequently formed at the original position of the amide group in a one‐pot manner. The amide directing group is detached simultaneously under the reaction conditions through C−C bond cleavage. Surprisngly, the distinct isoquinolinone products can be achieved by changing the reaction conditions using ammonia as amine source. |
| doi_str_mv | 10.1002/adsc.201901316 |
| format | Article |
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In this reaction, the C−C bond is successfully constructed via C−H activation, and C−O bond is subsequently formed at the original position of the amide group in a one‐pot manner. The amide directing group is detached simultaneously under the reaction conditions through C−C bond cleavage. Surprisngly, the distinct isoquinolinone products can be achieved by changing the reaction conditions using ammonia as amine source.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201901316</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>Ammonia ; benzofurans synthesis ; cascade reaction ; chemoselectivity ; Cleavage ; Copper ; C−H activation ; traceless directing group</subject><ispartof>Advanced synthesis & catalysis, 2020-01, Vol.362 (1), p.118-125</ispartof><rights>2020 Wiley‐VCH Verlag GmbH & Co. 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In this reaction, the C−C bond is successfully constructed via C−H activation, and C−O bond is subsequently formed at the original position of the amide group in a one‐pot manner. The amide directing group is detached simultaneously under the reaction conditions through C−C bond cleavage. Surprisngly, the distinct isoquinolinone products can be achieved by changing the reaction conditions using ammonia as amine source.</description><subject>Ammonia</subject><subject>benzofurans synthesis</subject><subject>cascade reaction</subject><subject>chemoselectivity</subject><subject>Cleavage</subject><subject>Copper</subject><subject>C−H activation</subject><subject>traceless directing group</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFkD9PwzAQxSMEEqWwMltigaGt7cROzNam9I9UxEA7R65zqVK1cbGTojIxMjAgPmI_CUmDyshyd9LvvXfSc5xrgtsEY9qRsVVtionAxCX8xGkQTljLI1ycHm-Gz50La5cYEz_w_YbzGRa34_Hd_v3rEeJU5hCjcP_xHXaq-YR6OovRQJu1zFOdoW0qD3h0wGGNwxXIrVzAPeoqBdaiXKMeZG86KYzMLJrZNFug7jqNAUmLJJoaqWBVKfupAZVXeGh0sbl0zhK5snD1u5vObPAwDUetydNwHHYnLeUyj7fmc05E4FIWS5IwnygGPgXpMyq8IKBzmAsXJ0oILqiULueYeoEfCAqYKCV8t-nc1Lkbo18KsHm01IXJypcRdV2PM15mlap2rVJGW2sgiTYmXUuziwiOqsajqvHo2HhpELXhNV3B7h911O0_h3_eH2B-huI</recordid><startdate>20200107</startdate><enddate>20200107</enddate><creator>Yu, Shuling</creator><creator>Lv, Ningning</creator><creator>Liu, Zhanxiang</creator><creator>Zhang, Yuhong</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20200107</creationdate><title>Cu(II)‐Mediated C−C/C−O Bond Formation via C−H/C−C Bond Cleavage: Access to Benzofurans Using Amide as a Traceless Directing Group</title><author>Yu, Shuling ; Lv, Ningning ; Liu, Zhanxiang ; Zhang, Yuhong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3546-bb6198325da1f571c5e72ea75294882beb930fc99692aa36602487892e01cc973</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Ammonia</topic><topic>benzofurans synthesis</topic><topic>cascade reaction</topic><topic>chemoselectivity</topic><topic>Cleavage</topic><topic>Copper</topic><topic>C−H activation</topic><topic>traceless directing group</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yu, Shuling</creatorcontrib><creatorcontrib>Lv, Ningning</creatorcontrib><creatorcontrib>Liu, Zhanxiang</creatorcontrib><creatorcontrib>Zhang, Yuhong</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yu, Shuling</au><au>Lv, Ningning</au><au>Liu, Zhanxiang</au><au>Zhang, Yuhong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cu(II)‐Mediated C−C/C−O Bond Formation via C−H/C−C Bond Cleavage: Access to Benzofurans Using Amide as a Traceless Directing Group</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2020-01-07</date><risdate>2020</risdate><volume>362</volume><issue>1</issue><spage>118</spage><epage>125</epage><pages>118-125</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>A copper‐mediated synthesis of 2,3‐disubstituted benzofurans with the assistance of an 8‐aminoquinolyl auxiliary is described from readily available benzamides and benzoylacetonitriles. In this reaction, the C−C bond is successfully constructed via C−H activation, and C−O bond is subsequently formed at the original position of the amide group in a one‐pot manner. The amide directing group is detached simultaneously under the reaction conditions through C−C bond cleavage. Surprisngly, the distinct isoquinolinone products can be achieved by changing the reaction conditions using ammonia as amine source.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.201901316</doi><tpages>8</tpages></addata></record> |
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| ispartof | Advanced synthesis & catalysis, 2020-01, Vol.362 (1), p.118-125 |
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| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Ammonia benzofurans synthesis cascade reaction chemoselectivity Cleavage Copper C−H activation traceless directing group |
| title | Cu(II)‐Mediated C−C/C−O Bond Formation via C−H/C−C Bond Cleavage: Access to Benzofurans Using Amide as a Traceless Directing Group |
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