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Rate Enhancement in CAN-Promoted Pd(PPh3)2Cl2-Catalyzed Oxidative Cyclization: Synthesis of 2-Ketofuran-4-carboxylate
Sureeporn Ruengsangtongkul1, Nattawadee Chaisan2, Charnsak Thongsornkleeb3,2
1Laboratory of Medicinal Chemistry , Chulabhorn Research Institute , 54 Kamphaeng Phet 6 , Laksi, Bangkok 10210 , Thailand.
Abstract:
Stoichiometric ceric ammonium nitrate (CAN) and a catalytic amount of Pd(PPh3)2Cl2 (5 mol %) can rapidly produce multisubstituted 2-ketofuran-4-carboxylate esters from 2-propargylic 1,3-ketoesters via oxidative O-cyclization reaction. Pd(PPh3)2Cl2 was found to be the crucial catalyst as its inclusion greatly enhanced the rate of the reaction and cleanly afforded the products within minutes. Over 30 substrates were successfully converted to the desired compounds in mostly moderate to good yields.
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