Indium(III) Trifluoromethanesulfonate as an Efficient Catalyst for the Deprotection of Acetals and Ketals

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Abstract

Acetals and ketals are readily deprotected under neutral conditions in the presence of acetone and catalytic amounts of indium(III) trifluoromethanesulfonate (<0.8 mol %) at room temperature or mild microwave heating conditions to give the corresponding aldehydes and ketones in good to excellent yields.

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This article has been cited by 3 ACS Journal articles (3 most recent appear below).

• 

  A Solvent-Free Method for Making Dioxolane and Dioxane from the Biorenewables Glycerol and Furfural Catalyzed by Oxorhenium(V) Oxazoline

  Benjamin L. Wegenhart and Mahdi M. Abu-Omar
  Inorganic Chemistry2010 49 (11), 4741-4743

  • A Solvent-Free Method for Making Dioxolane and Dioxane from the Biorenewables Glycerol and Furfural Catalyzed by Oxorhenium(V) Oxazoline

    Benjamin L. Wegenhart and Mahdi M. Abu-Omar
    Inorganic Chemistry2010 49 (11), 4741-4743

    Low catalyst loading of a cationic oxorhenium(V) oxazoline complex, [2-(2′-hydroxyphenyl)-2-oxazolinato(−2)]oxorhenium(v), condenses diols and aldehydes to give 1,3-dioxolanes in excellent yields under neat conditions and reasonably mild temperatures. The ...

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

  Mechanistic Pathways in CF₃COOH-Mediated Deacetalization Reactions

  Wei Li, Jianchang Li, Yuchuan Wu, Nathan Fuller and Michelle A. Markus
  The Journal of Organic Chemistry2010 75 (4), 1077-1086

  • Mechanistic Pathways in CF₃COOH-Mediated Deacetalization Reactions

    Wei Li, Jianchang Li, Yuchuan Wu, Nathan Fuller and Michelle A. Markus
    The Journal of Organic Chemistry2010 75 (4), 1077-1086

    It has been widely accepted that both the protection of carbonyls and the deprotection of acetals and ketals involve the participation of a water molecule: formation of acetals and ketals is a dehydration process, whereas the deprotection is often ...

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

  Expedient Lewis Acid Catalyzed Synthesis of a 3-Substituted 5-Arylidene-1-methyl-2-thiohydantoin Library

  Brian T. Gregg, Kathryn C. Golden, John F. Quinn, Dmytro O. Tymoshenko, William G. Earley, Dacia A. Maynard, Dana A. Razzano, W. Martin Rennells and Jennifer Butcher
  Journal of Combinatorial Chemistry2007 9 (6), 1036-1040

  • Expedient Lewis Acid Catalyzed Synthesis of a 3-Substituted 5-Arylidene-1-methyl-2-thiohydantoin Library

    Brian T. Gregg, Kathryn C. Golden, John F. Quinn, Dmytro O. Tymoshenko, William G. Earley, Dacia A. Maynard, Dana A. Razzano, W. Martin Rennells and Jennifer Butcher
    Journal of Combinatorial Chemistry2007 9 (6), 1036-1040

    An efficient and rapid solution phase combinatorial synthesis of a 3-substituted 5-arylidene-1-methyl-2-thiohydantoin library was developed. The salient feature for this library production procedure is the addition of the Lewis acid catalyst, indium(III) ...

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

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