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

Author:
Min, Hongkeun, Palani, Thiruvengadam, Park, Kyungho, Hwang, Jinil, Lee, Sunwoo
Source:
Journal of organic chemistry 2014 v.79 no.13 pp. 6279-6285
ISSN:
1520-6904
Subject:
aldehydes, catalysts, copper, iodides, moieties, organic chemistry, oxidation, palladium, propionates
Abstract:
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 °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.
Agid:
5502453