Rhodium-Catalyzed Interconversion of Quinolinyl Ketones with Boronic Acids via C–C Bond Activation

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• 作者：Joseph M. Dennis ; Chad T. Compagner ; Stanna K. Dorn ; Jeffrey B. Johnson
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：July 15, 2016
• 年：2016
• 卷：18
• 期：14
• 页码：3334-3337
• 全文大小：304K
• 年卷期：0
• ISSN：1523-7052

文摘

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(PPhb>3b>)b>3b>Cl instead of the more reactive [Rh(Cb>2b>Hb>4b>)b>2b>Cl]b>2b>. With the use of Kb>2b>COb>3b> as an additive, methyl boronic acid is also a competent substrate, giving rise to an unprecedented methylation technique.