Silver-Catalyzed Highly Regioselective Synthesis of<font>α</font>-Carbonyl Furans from Enynones

Abstract

Abstract A general and efficient method for the synthesis of a wide range of α-carbonyl furans is described here. The cyclization of enynone is catalyzed by AgBF4 in a fluorous biphasic system of perfluorodecalin and N,N-dimethylformamide. A variety of chain ketone and cyclic ketone substrates were used to investigate the scope of the reactions. Keywords: α-Carbonyl furansenynoneketonemolecular oxygenperfluorodecalin Notes a Reaction conditions: 1a (0.25 mmol), catalyst (10 mol%), O2 (1 atm), cosolvent (0.5 mL), and perfluorodecalin (0.5 mL) at 60 °C for 16 h. b Determined by GC. Number in parentheses is isolated yield. c DMF (1 mL) without perfluorodecalin. d Under anaerobic conditions. e AgBF4 (3 mol%). a The reactions were carried out with 1 (0.25 mmol), AgBF4 (10 mol%), O2 (1 atm), DMF (0.5 mL), and perfluorodecalin (0.5 mL) at 60 °C for 16 h.