Ruthenium(II)‐Catalyzed C−H Activation/Annulation of Aromatic Hydroxamic Acid Esters with Enamides Leading to Aminal Motifs
Hydroxamic acid ester directed C(sp2)−H activation/annulation strategy has been reported employing electron‐rich enamides under Ru(II)‐catalysis to access aminal frameworks. Both N‐vinyl acetamide and N‐vinyl formamide delivered aminals bearing dihydroisoquinolinone motif in good yields. Under modif...
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| Veröffentlicht in: | European journal of organic chemistry 2021-03, Vol.2021 (9), p.1385-1389 |
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| container_end_page | 1389 |
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| container_issue | 9 |
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| container_title | European journal of organic chemistry |
| container_volume | 2021 |
| creator | Dana, Suman Sureshbabu, Popuri Giri, Chandan Kumar Baidya, Mahiuddin |
| description | Hydroxamic acid ester directed C(sp2)−H activation/annulation strategy has been reported employing electron‐rich enamides under Ru(II)‐catalysis to access aminal frameworks. Both N‐vinyl acetamide and N‐vinyl formamide delivered aminals bearing dihydroisoquinolinone motif in good yields. Under modified reaction conditions, vinyl acetate bestowed the selective formation of 3,4‐unsubstituted isoquinolones. The protocol operates under mild conditions, where the C−H ruthenation step is reversible and apparently not the rate‐determining step.
An annulative coupling between aromatic hydroxamic acid esters and electron‐rich olefins such as enamides has been developed for the production of valuable aminal frameworks under inexpensive ruthenium catalysis. |
| doi_str_mv | 10.1002/ejoc.202001632 |
| format | Article |
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An annulative coupling between aromatic hydroxamic acid esters and electron‐rich olefins such as enamides has been developed for the production of valuable aminal frameworks under inexpensive ruthenium catalysis.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.202001632</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Aminals ; Annulation ; Chemical reactions ; C−H Activation ; Esters ; Homogeneous catalysis ; Organic chemistry ; Ruthenium ; Ruthenium compounds ; Vinyl acetate</subject><ispartof>European journal of organic chemistry, 2021-03, Vol.2021 (9), p.1385-1389</ispartof><rights>2021 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3172-bab0c394e2886f1915dac01e004a511e403d282eac1edbe3d23b7b0e0b8a1fb23</citedby><cites>FETCH-LOGICAL-c3172-bab0c394e2886f1915dac01e004a511e403d282eac1edbe3d23b7b0e0b8a1fb23</cites><orcidid>0000-0001-9415-7137</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejoc.202001632$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.202001632$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Dana, Suman</creatorcontrib><creatorcontrib>Sureshbabu, Popuri</creatorcontrib><creatorcontrib>Giri, Chandan Kumar</creatorcontrib><creatorcontrib>Baidya, Mahiuddin</creatorcontrib><title>Ruthenium(II)‐Catalyzed C−H Activation/Annulation of Aromatic Hydroxamic Acid Esters with Enamides Leading to Aminal Motifs</title><title>European journal of organic chemistry</title><description>Hydroxamic acid ester directed C(sp2)−H activation/annulation strategy has been reported employing electron‐rich enamides under Ru(II)‐catalysis to access aminal frameworks. Both N‐vinyl acetamide and N‐vinyl formamide delivered aminals bearing dihydroisoquinolinone motif in good yields. Under modified reaction conditions, vinyl acetate bestowed the selective formation of 3,4‐unsubstituted isoquinolones. The protocol operates under mild conditions, where the C−H ruthenation step is reversible and apparently not the rate‐determining step.
An annulative coupling between aromatic hydroxamic acid esters and electron‐rich olefins such as enamides has been developed for the production of valuable aminal frameworks under inexpensive ruthenium catalysis.</description><subject>Aminals</subject><subject>Annulation</subject><subject>Chemical reactions</subject><subject>C−H Activation</subject><subject>Esters</subject><subject>Homogeneous catalysis</subject><subject>Organic chemistry</subject><subject>Ruthenium</subject><subject>Ruthenium compounds</subject><subject>Vinyl acetate</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFkDFPwzAQhSMEEqWwMltigSHt2UnTeIyiQouKkBBIbJHjXMBVEoPtUMoCIyPiJ_JLCBTByHTfO713Oj3P26cwoABsiAstBwwYAI0CtuH1KHDuQ8Rhs-MwCH3Kg-ttb8faBQDwKKI97_midbfYqLY-nM2OPl7eUuFEtXrCgqQfr-9TkkinHoRTuhkmTdNW30h0SRKj605IMl0VRj-KusNEqoJMrENjyVK5WzJpun2BlsxRFKq5IU6TpFaNqMiZdqq0u95WKSqLez-z710dTy7TqT8_P5mlydyXAR0zPxc5yICHyOI4Kimno0JIoAgQihGlGEJQsJihkBSLHDsR5OMcEPJY0DJnQd87WN-9M_q-ReuyhW5N94fNWMgjHo1GMe9cg7VLGm2twTK7M6oWZpVRyL5Kzr5Kzn5L7gJ8HViqClf_uLPJ6Xn6l_0EqYmDqg</recordid><startdate>20210305</startdate><enddate>20210305</enddate><creator>Dana, Suman</creator><creator>Sureshbabu, Popuri</creator><creator>Giri, Chandan Kumar</creator><creator>Baidya, Mahiuddin</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-9415-7137</orcidid></search><sort><creationdate>20210305</creationdate><title>Ruthenium(II)‐Catalyzed C−H Activation/Annulation of Aromatic Hydroxamic Acid Esters with Enamides Leading to Aminal Motifs</title><author>Dana, Suman ; Sureshbabu, Popuri ; Giri, Chandan Kumar ; Baidya, Mahiuddin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3172-bab0c394e2886f1915dac01e004a511e403d282eac1edbe3d23b7b0e0b8a1fb23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Aminals</topic><topic>Annulation</topic><topic>Chemical reactions</topic><topic>C−H Activation</topic><topic>Esters</topic><topic>Homogeneous catalysis</topic><topic>Organic chemistry</topic><topic>Ruthenium</topic><topic>Ruthenium compounds</topic><topic>Vinyl acetate</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dana, Suman</creatorcontrib><creatorcontrib>Sureshbabu, Popuri</creatorcontrib><creatorcontrib>Giri, Chandan Kumar</creatorcontrib><creatorcontrib>Baidya, Mahiuddin</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dana, Suman</au><au>Sureshbabu, Popuri</au><au>Giri, Chandan Kumar</au><au>Baidya, Mahiuddin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ruthenium(II)‐Catalyzed C−H Activation/Annulation of Aromatic Hydroxamic Acid Esters with Enamides Leading to Aminal Motifs</atitle><jtitle>European journal of organic chemistry</jtitle><date>2021-03-05</date><risdate>2021</risdate><volume>2021</volume><issue>9</issue><spage>1385</spage><epage>1389</epage><pages>1385-1389</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>Hydroxamic acid ester directed C(sp2)−H activation/annulation strategy has been reported employing electron‐rich enamides under Ru(II)‐catalysis to access aminal frameworks. Both N‐vinyl acetamide and N‐vinyl formamide delivered aminals bearing dihydroisoquinolinone motif in good yields. Under modified reaction conditions, vinyl acetate bestowed the selective formation of 3,4‐unsubstituted isoquinolones. The protocol operates under mild conditions, where the C−H ruthenation step is reversible and apparently not the rate‐determining step.
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| ispartof | European journal of organic chemistry, 2021-03, Vol.2021 (9), p.1385-1389 |
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| language | eng |
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| subjects | Aminals Annulation Chemical reactions C−H Activation Esters Homogeneous catalysis Organic chemistry Ruthenium Ruthenium compounds Vinyl acetate |
| title | Ruthenium(II)‐Catalyzed C−H Activation/Annulation of Aromatic Hydroxamic Acid Esters with Enamides Leading to Aminal Motifs |
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