Copper(II)-Catalyzed Sequential C,N-Difunctionalization of 1,4-Naphthoquinone for the Synthesis of Benzo[f]indole-4,9-diones under Base-Free Condition
An efficient synthesis of benzo[f]indole-4,9-diones has been achieved by copper(II)-catalyzed naphthoquinone sequential C,N-difunctionalization reactions with β-enaminones. New C–C and C–N bonds are easily formed in the reaction course. Copper(II) salt plays a dual role as Lewis acid and oxidative c...
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| Veröffentlicht in: | Journal of organic chemistry 2013-10, Vol.78 (20), p.10560-10566 |
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| container_end_page | 10566 |
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| container_issue | 20 |
| container_start_page | 10560 |
| container_title | Journal of organic chemistry |
| container_volume | 78 |
| creator | Sun, Jin-Wei Wang, Xiang-Shan Liu, Yun |
| description | An efficient synthesis of benzo[f]indole-4,9-diones has been achieved by copper(II)-catalyzed naphthoquinone sequential C,N-difunctionalization reactions with β-enaminones. New C–C and C–N bonds are easily formed in the reaction course. Copper(II) salt plays a dual role as Lewis acid and oxidative catalyst, and O2 acts as the terminal oxidant. The advantage of this reaction is the high atom economy with broad substrate scope and excellent yields. The reaction can be scaled up to using at least grams of substrates. |
| doi_str_mv | 10.1021/jo401842d |
| format | Article |
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New C–C and C–N bonds are easily formed in the reaction course. Copper(II) salt plays a dual role as Lewis acid and oxidative catalyst, and O2 acts as the terminal oxidant. The advantage of this reaction is the high atom economy with broad substrate scope and excellent yields. The reaction can be scaled up to using at least grams of substrates.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo401842d</identifier><identifier>PMID: 24070011</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Catalysis ; Copper - chemistry ; Indoles - chemical synthesis ; Indoles - chemistry ; Lewis Acids - chemistry ; Molecular Structure ; Naphthoquinones - chemistry ; Oxidation-Reduction</subject><ispartof>Journal of organic chemistry, 2013-10, Vol.78 (20), p.10560-10566</ispartof><rights>Copyright © 2013 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a315t-d0bb07844ed92c6e22adf92c694a4298d5d054e075eda0112ea2d4658224953d3</citedby><cites>FETCH-LOGICAL-a315t-d0bb07844ed92c6e22adf92c694a4298d5d054e075eda0112ea2d4658224953d3</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/jo401842d$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo401842d$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24070011$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sun, Jin-Wei</creatorcontrib><creatorcontrib>Wang, Xiang-Shan</creatorcontrib><creatorcontrib>Liu, Yun</creatorcontrib><title>Copper(II)-Catalyzed Sequential C,N-Difunctionalization of 1,4-Naphthoquinone for the Synthesis of Benzo[f]indole-4,9-diones under Base-Free Condition</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>An efficient synthesis of benzo[f]indole-4,9-diones has been achieved by copper(II)-catalyzed naphthoquinone sequential C,N-difunctionalization reactions with β-enaminones. New C–C and C–N bonds are easily formed in the reaction course. Copper(II) salt plays a dual role as Lewis acid and oxidative catalyst, and O2 acts as the terminal oxidant. The advantage of this reaction is the high atom economy with broad substrate scope and excellent yields. The reaction can be scaled up to using at least grams of substrates.</description><subject>Catalysis</subject><subject>Copper - chemistry</subject><subject>Indoles - chemical synthesis</subject><subject>Indoles - chemistry</subject><subject>Lewis Acids - chemistry</subject><subject>Molecular Structure</subject><subject>Naphthoquinones - chemistry</subject><subject>Oxidation-Reduction</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkb9OwzAQhy0EglIYeAHkBQmkGmzHbpMRwr9KFQzAhFDkxhfVKLVTOxnaB-F5cVRg4pa74btPuvshdMLoJaOcXX06QVkquN5BAyY5JeOMil00oJRzkvBxcoAOQ_iksaSU--iACzqhlLEB-spd04A_n04vSK5aVa83oPELrDqwrVE1zkdP5NZUnS1b46yqzUb1A3YVZiNBnlSzaBdu1RnrLODKedwuAL-sbWzBhJ67Abtx79WHsdrVQMQoIzoqIODOavD4RgUg9x4A585q0-uP0F6l6gDHP32I3u7vXvNHMnt-mObXM6ISJlui6XxOJ6kQoDNejoFzpat-yoQSPEu11FQKoBMJWsV7OSiuxVimnItMJjoZovOtt_HxBghtsTShhLpWFlwXCiZEItgklSyiF1u09C4ED1XReLNUfl0wWvQxFH8xRPb0R9vNl6D_yN-_R-BsC6gyxL3Ox8-Gf0TfAEOOiw</recordid><startdate>20131018</startdate><enddate>20131018</enddate><creator>Sun, Jin-Wei</creator><creator>Wang, Xiang-Shan</creator><creator>Liu, Yun</creator><general>American Chemical Society</general><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>20131018</creationdate><title>Copper(II)-Catalyzed Sequential C,N-Difunctionalization of 1,4-Naphthoquinone for the Synthesis of Benzo[f]indole-4,9-diones under Base-Free Condition</title><author>Sun, Jin-Wei ; Wang, Xiang-Shan ; Liu, Yun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a315t-d0bb07844ed92c6e22adf92c694a4298d5d054e075eda0112ea2d4658224953d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Catalysis</topic><topic>Copper - chemistry</topic><topic>Indoles - chemical synthesis</topic><topic>Indoles - chemistry</topic><topic>Lewis Acids - chemistry</topic><topic>Molecular Structure</topic><topic>Naphthoquinones - chemistry</topic><topic>Oxidation-Reduction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sun, Jin-Wei</creatorcontrib><creatorcontrib>Wang, Xiang-Shan</creatorcontrib><creatorcontrib>Liu, Yun</creatorcontrib><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>Sun, Jin-Wei</au><au>Wang, Xiang-Shan</au><au>Liu, Yun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper(II)-Catalyzed Sequential C,N-Difunctionalization of 1,4-Naphthoquinone for the Synthesis of Benzo[f]indole-4,9-diones under Base-Free Condition</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2013-10-18</date><risdate>2013</risdate><volume>78</volume><issue>20</issue><spage>10560</spage><epage>10566</epage><pages>10560-10566</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>An efficient synthesis of benzo[f]indole-4,9-diones has been achieved by copper(II)-catalyzed naphthoquinone sequential C,N-difunctionalization reactions with β-enaminones. New C–C and C–N bonds are easily formed in the reaction course. Copper(II) salt plays a dual role as Lewis acid and oxidative catalyst, and O2 acts as the terminal oxidant. The advantage of this reaction is the high atom economy with broad substrate scope and excellent yields. The reaction can be scaled up to using at least grams of substrates.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>24070011</pmid><doi>10.1021/jo401842d</doi><tpages>7</tpages></addata></record> |
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| language | eng |
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| source | MEDLINE; American Chemical Society Web Editions |
| subjects | Catalysis Copper - chemistry Indoles - chemical synthesis Indoles - chemistry Lewis Acids - chemistry Molecular Structure Naphthoquinones - chemistry Oxidation-Reduction |
| title | Copper(II)-Catalyzed Sequential C,N-Difunctionalization of 1,4-Naphthoquinone for the Synthesis of Benzo[f]indole-4,9-diones under Base-Free Condition |
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