Catalytic Formation of Ketones from Unactivated Esters through Rhodium Chelation-Assisted C鈥揙 Bond Activation

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• 作者：Jingjing Wang ; Sujing Zuo ; Weiqiang Chen ; Xinrui Zhang ; Kaixin Tan ; Yun Tian ; Jianhui Wang
• 刊名：Journal of Organic Chemistry
• 出版年：2013
• 出版时间：September 6, 2013
• 年：2013
• 卷：78
• 期：17
• 页码：8217-8231
• 全文大小：559K
• 年卷期：v.78,no.17(September 6, 2013)
• ISSN：1520-6904

文摘

A new method for building aryl aryl ketones containing heterocyclic rings through chelation-assisted C鈥揙 bond activation catalyzed by a rhodium complex has been developed. In this reaction, methyl quinoline-8-carboxylate, methyl quinoxaline-5-carboxylate, and their derivatives were reacted with an excess amount of a substituted phenyl boronic acid in the presence of a rhodium(I) complex to give substituted phenyl(quinolin-8-yl)methanone, phenylquinoxalin-5-ylmethanone, and their derivatives in medium to high yields. The current method offers a highly favorable synthetic pathway to efficiently build related drugs with an 8-benzoylquinoline core structure. This method may prove especially valuable for medicinal chemists for the late-stage introduction of versatile ketone moieties into complex scaffolds for diversity-oriented synthetic strategies.