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Article
Synthesis of Trifluoromethyl-Imines by Solid Acid/Superacid Catalyzed Microwave-Assisted Approach
Journal of Fluorine Chemistry (2007)
  • Mohammed Abid, University of Massachusetts, Boston
  • Markku Savolainen, Michigan Technological University
  • Shainaz M. Landge, University of Massachusetts
  • Jinbo Hu, University of Southern California, University Park
  • G.K. S. Prakash, University of Southern California, University Park,
  • George A. Olah, University of Southern California, University Park,
  • Béla Török, University of Massachusetts Boston
Abstract
A new solid acid/superacid catalyzed microwave assisted synthesis of trifluoromethyl-imines is described. Various α,α,α-trifluoromethylketones react readily with primary amines to produce the corresponding imines. Two different strategies have been employed; one is the application of microwave irradiation coupled with solvent-free solid acid catalysis. The other method, for highly deactivated substrates includes the use of a pressure vessel at 175 °C temperature, with solid superacid catalysis. Using the solid acid K-10 montmorillonite or the superacidic perfluorinated resinsulfonic acid Nafion-H, a wide variety of trifluoromethylated imines have been synthesized using the above methods. The products have been isolated in good to excellent yields and high selectivities. This new environmentally friendly synthetic methodology provides significantly higher yields than traditional methods during relatively short reaction times for the preparation of the target compounds.
Keywords
  • Trifluoromethyl,
  • Imine,
  • Clay,
  • Solid acids,
  • Solid superacid,
  • Catalysis,
  • Microwave irradiation
Disciplines
Publication Date
June, 2007
DOI
10.1016/j.jfluchem.2007.01.011
Publisher Statement
This is an Accepted Author Manuscript obtained from the PMC. The publisher's final edited version of this article is available at the Journal of Fluorine Chemistry.
Citation Information
Mohammed Abid, Markku Savolainen, Shainaz M. Landge, Jinbo Hu, et al.. "Synthesis of Trifluoromethyl-Imines by Solid Acid/Superacid Catalyzed Microwave-Assisted Approach" Journal of Fluorine Chemistry Vol. 128 Iss. 6 (2007) p. 587 - 594
Available at: http://works.bepress.com/shainaz_landge/45/