Copper-Catalyzed Direct Synthesis of Diaryl 1,2-Diketones from Aryl Iodides and Propiolic Acids

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• 作者：Hongkeun Min ; Thiruvengadam Palani ; Kyungho Park ; Jinil Hwang ; Sunwoo Lee
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：July 3, 2014
• 年：2014
• 卷：79
• 期：13
• 页码：6279-6285
• 全文大小：320K
• ISSN：1520-6904

文摘

Benzil derivatives such as diaryl 1,2-diketones are synthesized via the direct decarboxylative coupling reaction of aryl propiolic acids and their oxidation. The optimized conditions are that the reaction of aryl propiolic acids and aryl iodides is conducted at 140 掳C for 6 h in the presence of 10 mol % CuI/Cu(OTf)₂ and Cs₂CO₃, after which HI (aq) is added and further reacted. The method shows good functional group tolerance toward ester, aldehyde, cyano, and nitro groups. In addition, symmetrical diaryl 1,2-diketones are obtained from aryl iodides and propiolic acid in the presence of palladium and copper catalysts.