Wacker Oxidation

J. Smidt et al., Angew. Chem. Int. Ed. 1, 176 (1959).

The oxidation of ethylene to employing palladium chloride and cupric chloride as catalysts and molecular oxygen as oxidant. The reaction has been extensively developed for the oxidation of terminal alkenes to methyl ketones:



Application to hydroxy-α,β-unsaturated esters: S. X. Auclair et al., Tetrahedron Letters 33, 7739 (1992). Use of a multicomponent catalytic system: E. Monflier et al., ibid. 36, 387 (1995). Synthetic applications: M. Romero et al., ibid. 35, 3255 (1994); L. A. Paquette, X. Wang, J. Org. Chem. 59, 2052 (1994). Reviews: L. S. Hegedus, Comp. Org. Syn. 4, 552-559 (1991); J. Tsuji, ibid. 6, 449-468.