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  • 00 Wacker-Tsuji Oxidation

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    The Wacker-Tsuji oxidation is a palladium-catalyzed reaction that uses molecular oxygen or water as the oxygen source to oxidize alkenes and alkynes into ketones. It is an industrial process for producing acetaldehyde from ethylene. In the lab, it is useful for synthesizing various ketones. The mechanism involves palladium facilitating the addition of oxygen across the carbon-carbon double bond, and copper serving as a redox co-catalyst to reoxidize reduced palladium.

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    The Wacker-Tsuji oxidation is a palladium-catalyzed reaction that uses molecular oxygen or water as the oxygen source to oxidize alkenes and alkynes into ketones. It is an industrial process for producing acetaldehyde from ethylene. In the lab, it is useful for synthesizing various ketones. The mechanism involves palladium facilitating the addition of oxygen across the carbon-carbon double bond, and copper serving as a redox co-catalyst to reoxidize reduced palladium.

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    Attribution Non-Commercial (BY-NC)
    Download as PDF, TXT or read online from Scribd
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    60 views2 pages

    00 Wacker-Tsuji Oxidation

    Uploaded by

    Văn Đại - BKHN
    The Wacker-Tsuji oxidation is a palladium-catalyzed reaction that uses molecular oxygen or water as the oxygen source to oxidize alkenes and alkynes into ketones. It is an industrial process for producing acetaldehyde from ethylene. In the lab, it is useful for synthesizing various ketones. The mechanism involves palladium facilitating the addition of oxygen across the carbon-carbon double bond, and copper serving as a redox co-catalyst to reoxidize reduced palladium.

    Copyright:

    Attribution Non-Commercial (BY-NC)
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    Wacker-Tsuji Oxidation

    http://www.organic-chemistry.org/namedreactions...

    Organic Chemistry Portal Reactions >> Name Reactions

    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.

    Convenient and Efficient Pd-Catalyzed Regioselective Oxyfunctionalization of Terminal Olefins by Using Molecular Oxygen as

    1z2

    07.12.2010 11:46

    Wacker-Tsuji Oxidation

    http://www.organic-chemistry.org/namedreactions...

    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 CrossCoupling A. N. Thadani, V. H. Rawal, Org. Lett., 2002 , 4 , 4321-4323.

    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.

    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.

    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.

    2z2

    07.12.2010 11:46

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