Wacker oxidation of alkenes using a fluorous biphasic system. A mild preparation of polyfunctional ketones

B Betzemeier, F Lhermitte, P Knochel

Index: Betzemeier, Bodo; Lhermitte, Frederic; Knochel, Paul Tetrahedron Letters, 1998 , vol. 39, # 37 p. 6667 - 6670

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Citation Number: 76

Abstract

A 25 mL-flask was charged with the diketone 6 (3.23 g, 4.0 mmol) dissolved in CH 2 Cl 2 /THF (3:1, 3 mL). After addition of palladium(II) acetate (0.45 g, 2.0 mmol, 0.5 equiv) the reaction mixture was stirred for 3 h and the orange precipitate was filtrated yielding pure palladium bis(diketonate) (3: 2.69 g, 78 % yield). 1 H-NMR (THF-d 8 , 300 MHz): δ = 6.09 (s, 2H); 13 C-NMR (THF-d 8 , 75 MHz): δ = 179.4 (t, J = 23 Hz, 120.0-108.7 (m), 92.8 (s).