Further Information
Literature
Related Reactions
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.
Pd-Catalyzed TBHP-Mediated Selective Wacker-Type Oxidation and
Oxo-acyloxylation of Olefins Using a 2-(1H-Indazol-1-yl)quinoline Ligand
S. Zhang, J. Zhang, H. Zou, Org. Lett., 2023, 25,
1850-1855.
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.
Selective Oxidation of Styrene Derivatives to Ketones over
Palladium(0)/Carbon with Hydrogen Peroxide as the Sole Oxidant
X. Xia, X. Gao, J. Xu, C. Hu, X. Peng,
Synlett, 2017, 28, 607-610.
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.