Further Information
Literature
Wacker-Tsuji Oxidation
The Wacker Oxidation is an industrial process, which allows the synthesis of ethanal from ethene by palladium-catalyzed oxidation with oxygen. Copper serves as redox cocatalyst.
The lab scale modification - the Wacker-Tsuji Oxidation - is useful for the synthesis of various ketones.
Mechanism
The mechanism is typical of palladium olefin chemistry, and water serves as the oxygen source; the reduced palladium is reoxidized by Cu(II) and ultimately by atmospheric oxygen.
J. Tsuji, "Palladium Reagents and Catalysts", First Edition 2004, Wiley, 29-35.
Recent Literature
Discovery of a Practical Direct O2-Coupled Wacker
Oxidation with Pd[(-)-sparteine]Cl2
C. N. Cornell, M. S. Sigman, Org. Lett., 2006, 8, 4117-4120.
Convenient and Efficient Pd-Catalyzed Regioselective Oxyfunctionalization of
Terminal Olefins by Using Molecular Oxygen as Sole Reoxidant
T. Mitsudome, T. Umetani, N. Nosaka, K. Mori, T. Mizugaki, K. Ebitani, K.
Kaneda, Angew. Chem. Int. Ed., 2006, 45, 481-485.
Multifunctional Palladium Catalysis. 2. Tandem Haloallylation Followed by
Wacker-Tsuji Oxidation or Sonogashira Cross-Coupling
A. N. Thadani, V. H. Rawal, Org. Lett., 2002, 4, 4321-4323.
Multicatalytic Processes Using Diverse Transition Metals for the Synthesis
of Alkenes
H. Lebel, V. Paquet, J. Am. Chem. Soc., 2004, 126, 11152-11153.
