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Oxidation of Alkenes

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 of the Wacker-Tsuji Oxidation

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.

Wacker-Type Oxidation and Dehydrogenation of Terminal Olefins Using Molecular Oxygen as the Sole Oxidant without Adding Ligand
Y.-F. Wang, Y.-R. Gao, S. Mao, Y.-L. Zhang, D.-D. Guo, Z.-L. Yan, S.-H. Guo, Y.-Q. Wang, Org. Lett., 2014, 16, 1610-1613.

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.

Hypervalent Iodine as a Terminal Oxidant in Wacker-Type Oxidation of Terminal Olefins to Methyl Ketones
D. A. Chaudhari, R. A. Fernandes, J. Org. Chem., 2016, 81, 2113-2121.

tert-Butyl Nitrite: Organic Redox Cocatalyst for Aerobic Aldehyde-Selective Wacker-Tsuji Oxidation
X.-S. Ning, M.-M. Wang, C.-Z. Yao, X.-M. Chen, Y.-B. Kang, Org. Lett., 2016, 18, 2700-2703.

Efficient and Highly Aldehyde Selective Wacker Oxidation
P. Teo, Z. K. Wickens, G. Dong, R. H. Grubbs, Org. Lett., 2012, 14, 3237-3239.

A General and Efficient Catalyst System for a Wacker-Type Oxidation Using TBHP as the Terminal Oxidant: Application to Classically Challenging Substrates
B. W. Michel, A. M. Camelio, C. N. Cornell, M. S. Sigman, J. Am. Chem. Soc., 2009, 131, 6076-6077.

Traceless OH-Directed Wacker Oxidation-Elimination, an Alternative to Wittig Olefination/Aldol Condensation: One-Pot Synthesis of α,β-Unsaturated and Nonconjugated Ketones from Homoallyl Alcohols
V. Bethi, R. A. Fernandes, J. Org. Chem., 2016, 81, 8577-8584.

Wacker-Type Oxidation of Internal Alkenes using Pd(Quinox) and TBHP
R. J. DeLuca, J. L. Edwards, L. D. Steffens, B. W. Michel, X. Qiao, C. Zhu, S. P. Cook, M. S. Sigman, J. Org. Chem., 2013, 78, 1682-1683.

Catalyst-Controlled Wacker-Type Oxidation: Facile Access to Functionalized Aldehydes
Z. K. Wickens, K. Skakuj, B. Morandi, R. H. Grubbs, J. Am. Chem. Soc., 2014, 136, 890-893.

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.

Wacker-Type Oxidation of Alkynes into 1,2-Diketones Using Molecular Oxygen
W. Ren, Y. Xia, S.-J. Ji, Y. Zhang, X. Wan, J. Zhao, Org. Lett., 2009, 11, 1841-1844.

Intramolecular Pd(II)-Catalyzed Aerobic Oxidative Amination of Alkenes: Synthesis of Six-Membered N-Heterocycles
Z. Lu, S. S. Stahl, Org. Lett., 2012, 14, 1234-1237.

A Facile Synthesis of 2-Methylquinolines via Pd-Catalyzed Aza-Wacker Oxidative Cyclization
Z. Zhang, J. Tang, Z. Wang, Org. Lett., 2008, 10, 173-175.