Selective Aerobic Oxidation of Activated Alcohols into Acids or Aldehydes in Ionic Liquids

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Abstract

Selective aerobic oxidation of activated primary alcohols into acids or aldehydes has been developed in ionic liquids. Under optimal conditions, various alcohols could be selectively converted into their corresponding acids or aldehydes in good to excellent yields. The newly developed catalytic systems could also be recycled and reused for three runs without any significant loss of catalytic activity.

Citing Articles

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This article has been cited by 8 ACS Journal articles (5 most recent appear below).

• 

  Selective Oxidation of Unsaturated Alcohols Catalyzed by Sodium Nitrite and 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone with Molecular Oxygen under Mild Conditions

  Lianyue Wang, Jun Li, Hua Yang, Ying Lv, and Shuang Gao
  The Journal of Organic Chemistry2012 77 (1), 790-794

  • Selective Oxidation of Unsaturated Alcohols Catalyzed by Sodium Nitrite and 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone with Molecular Oxygen under Mild Conditions

    Lianyue Wang, Jun Li, Hua Yang, Ying Lv, and Shuang Gao
    The Journal of Organic Chemistry2012 77 (1), 790-794

    We have developed a simple and practical process for the oxidation of alcohols to the corresponding carbonyl compounds by using a low catalytic amount of DDQ, NaNO2 as a cocatalyst, and molecular oxygen as terminal oxidant. Nitric oxide generated in situ ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Comparison of Copper and Vanadium Homogeneous Catalysts for Aerobic Oxidation of Lignin Models

  Baburam Sedai, Christian Díaz-Urrutia, R. Tom Baker, Ruilian Wu, L. A. “Pete” Silks, and Susan K. Hanson
  ACS Catalysis2011 Article ASAP

  • Comparison of Copper and Vanadium Homogeneous Catalysts for Aerobic Oxidation of Lignin Models

    Baburam Sedai, Christian Díaz-Urrutia, R. Tom Baker, Ruilian Wu, L. A. “Pete” Silks, and Susan K. Hanson
    ACS Catalysis2011 Article ASAP

    The reactivity of copper and vanadium catalysts toward the aerobic oxidation of lignin models has been explored. Both (dipic)VV(O)(OiPr) (3) (dipic = dipicolinate) and CuCl/TEMPO (TEMPO = tetramethylpiperidine N-oxide) catalyzed the aerobic oxidation of ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Room-Temperature Ionic Liquids: Solvents for Synthesis and Catalysis. 2

  Jason P. Hallett and Tom Welton
  Chemical Reviews2011 111 (5), 3508-3576

  • Room-Temperature Ionic Liquids: Solvents for Synthesis and Catalysis. 2

    Jason P. Hallett and Tom Welton
    Chemical Reviews2011 111 (5), 3508-3576
    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Mild and Selective Vanadium-Catalyzed Oxidation of Benzylic, Allylic, and Propargylic Alcohols Using Air

  Susan K. Hanson, Ruilian Wu, and L. A. “Pete” Silks
  Organic Letters2011 13 (8), 1908-1911

  • Mild and Selective Vanadium-Catalyzed Oxidation of Benzylic, Allylic, and Propargylic Alcohols Using Air

    Susan K. Hanson, Ruilian Wu, and L. A. “Pete” Silks
    Organic Letters2011 13 (8), 1908-1911

    Transition metal-catalyzed aerobic alcohol oxidation is an attractive method for the synthesis of carbonyl compounds, but most catalytic systems feature precious metals and require pure oxygen. The vanadium complex (HQ)2VV(O)(OiPr) (2 mol %, HQ = 8-...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Mechanism of Alcohol Oxidation by Dipicolinate Vanadium(V): Unexpected Role of Pyridine

  Susan K. Hanson, R. Tom Baker, John C. Gordon, Brian L. Scott, L. A. “Pete” Silks, and David L. Thorn
  Journal of the American Chemical Society2010 132 (50), 17804-17816

  • Mechanism of Alcohol Oxidation by Dipicolinate Vanadium(V): Unexpected Role of Pyridine

    Susan K. Hanson, R. Tom Baker, John C. Gordon, Brian L. Scott, L. A. “Pete” Silks, and David L. Thorn
    Journal of the American Chemical Society2010 132 (50), 17804-17816

    Dipicolinate vanadium(V) alkoxide complexes (dipic)VV(O)(OR) (OR = isopropoxide (1), n-butanoxide (2), cyclobutanoxide (3), and α-tert-butylbenzylalkoxide (4)) react with pyridine to afford vanadium(IV) and 0.5 equiv of an aldehyde or ketone product. The ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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