Rhodium-Catalyzed Interconversion of Quinolinyl Ketones with Boronic Acids via C–C Bond Activation
A rhodium-catalyzed cross-coupling of aryl and aliphatic quinolinyl ketones with boronic acids has been developed. Proceeding via quinoline-directed carbon–carbon σ bond activation, the transformation demonstrates tolerance of a range of functional groups on both the ketone and aryl boronic acid sub...
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| Veröffentlicht in: | Organic letters 2016-07, Vol.18 (14), p.3334-3337 |
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| container_title | Organic letters |
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| creator | Dennis, Joseph M Compagner, Chad T Dorn, Stanna K Johnson, Jeffrey B |
| description | A rhodium-catalyzed cross-coupling of aryl and aliphatic quinolinyl ketones with boronic acids has been developed. Proceeding via quinoline-directed carbon–carbon σ bond activation, the transformation demonstrates tolerance of a range of functional groups on both the ketone and aryl boronic acid substrates, providing good to excellent yields of the new ketones, particularly those containing electron-withdrawing substituents. Catalyst reactivity is dependent on quinolinyl ketone substrates, with alkyl ketones requiring Rh(PPh3)3Cl instead of the more reactive [Rh(C2H4)2Cl]2. With the use of K2CO3 as an additive, methyl boronic acid is also a competent substrate, giving rise to an unprecedented methylation technique. |
| doi_str_mv | 10.1021/acs.orglett.6b01434 |
| format | Article |
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Proceeding via quinoline-directed carbon–carbon σ bond activation, the transformation demonstrates tolerance of a range of functional groups on both the ketone and aryl boronic acid substrates, providing good to excellent yields of the new ketones, particularly those containing electron-withdrawing substituents. Catalyst reactivity is dependent on quinolinyl ketone substrates, with alkyl ketones requiring Rh(PPh3)3Cl instead of the more reactive [Rh(C2H4)2Cl]2. 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Lett</addtitle><description>A rhodium-catalyzed cross-coupling of aryl and aliphatic quinolinyl ketones with boronic acids has been developed. Proceeding via quinoline-directed carbon–carbon σ bond activation, the transformation demonstrates tolerance of a range of functional groups on both the ketone and aryl boronic acid substrates, providing good to excellent yields of the new ketones, particularly those containing electron-withdrawing substituents. Catalyst reactivity is dependent on quinolinyl ketone substrates, with alkyl ketones requiring Rh(PPh3)3Cl instead of the more reactive [Rh(C2H4)2Cl]2. With the use of K2CO3 as an additive, methyl boronic acid is also a competent substrate, giving rise to an unprecedented methylation technique.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNp9kE1OwzAUhC0EolA4ARLykk1a_8VJlhDxU1EJgWAdubYDRqkNtlNUVtyBG3ISXLV0yer5jWbGeh8AJxiNMCJ4LGQYOf_c6RhHfIYwo2wHHOCc0KxAOdndvjkagMMQXhHCSan2wYAUlBec0QOgHl6cMv08q0UU3fJTKzixUXvp7EL7YJyFroX3vbGuM3bZwVsdndUBfpj4Ai-cd9ZIeC6NCnBhBKx_vr7rpFuVxGgWIqaKI7DXii7o480cgqery8f6JpveXU_q82kmKMtjVvCCljyvdFoLwSql01FItaUiVOdSzGYFq9pClKXEmvCKM6KIZIqoSlRMcToEZ-veN-_eex1iMzdB6q4TVrs-NLhErOQ0L1Gy0rVVeheC123z5s1c-GWDUbPC2yS8zQZvs8GbUqebD_rZXKtt5o9nMozXhlX61fXepnv_rfwFCg2K2w</recordid><startdate>20160715</startdate><enddate>20160715</enddate><creator>Dennis, Joseph M</creator><creator>Compagner, Chad T</creator><creator>Dorn, Stanna K</creator><creator>Johnson, Jeffrey B</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20160715</creationdate><title>Rhodium-Catalyzed Interconversion of Quinolinyl Ketones with Boronic Acids via C–C Bond Activation</title><author>Dennis, Joseph M ; Compagner, Chad T ; Dorn, Stanna K ; Johnson, Jeffrey B</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-76738659ea347a49de0140df8d23e5cabb749f7a88c1e269642d2c4d2d9a94d63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dennis, Joseph M</creatorcontrib><creatorcontrib>Compagner, Chad T</creatorcontrib><creatorcontrib>Dorn, Stanna K</creatorcontrib><creatorcontrib>Johnson, Jeffrey B</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dennis, Joseph M</au><au>Compagner, Chad T</au><au>Dorn, Stanna K</au><au>Johnson, Jeffrey B</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Rhodium-Catalyzed Interconversion of Quinolinyl Ketones with Boronic Acids via C–C Bond Activation</atitle><jtitle>Organic letters</jtitle><addtitle>Org. 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With the use of K2CO3 as an additive, methyl boronic acid is also a competent substrate, giving rise to an unprecedented methylation technique.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>27367643</pmid><doi>10.1021/acs.orglett.6b01434</doi><tpages>4</tpages></addata></record> |
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| source | ACS Publications |
| title | Rhodium-Catalyzed Interconversion of Quinolinyl Ketones with Boronic Acids via C–C Bond Activation |
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