title: Copper-catalyzed direct synthesis of diaryl 1,2-diketones from aryl iodides and propiolic acids.
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.
authors: Department of Chemistry, Chonnam National University , Gwangju 500-757, Republic of Korea.
authors: Hongkeun
authors: H
authors: Min
authors: Thiruvengadam
authors: T
authors: Palani
authors: Kyungho
authors: K
authors: Park
authors: Jinil
authors: J
authors: Hwang
authors: Sunwoo
authors: S
authors: Lee
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D010658:Phenylglyoxal / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D011422:Propionates / Q000737:chemistry*
chemical_list: D000480:Alkynes; D007454:Iodides; D007659:Ketones; D011422:Propionates; D010165:Palladium; D003300:Copper; D010658:Phenylglyoxal; C011537:propiolic acid; C006697:benzil