Synergistic Effect of Two Solvents, tert-Alcohol and Ionic Liquid, in One Molecule in Nucleophilic Fluorination

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Abstract

We have demonstrated the synergistic effect in nucleophilic fluorination when we combined two solventsionic liquid (IL) and tert-alcoholinto one molecule. Consequently, these functionalized ILs not only increase the nucleophilic reactivities of the fluoride anion but also remarkably reduce the olefin byproduct. Although the mechanism of this synergistic effect remains to be elucidated, we have illustrated the possibility of solvent engineering for a specific reaction.

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

• 

  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
• 

  Toward Understanding the Origin of Positive Effects of Ionic Liquids on Catalysis: Formation of More Reactive Catalysts and Stabilization of Reactive Intermediates and Transition States in Ionic Liquids

  Ji Woong Lee, Ju Yeon Shin, Yu Sung Chun, Hyeong Bin Jang, Choong Eui Song and Sang-gi Lee
  Accounts of Chemical Research2010 43 (7), 985-994

  • Toward Understanding the Origin of Positive Effects of Ionic Liquids on Catalysis: Formation of More Reactive Catalysts and Stabilization of Reactive Intermediates and Transition States in Ionic Liquids

    Ji Woong Lee, Ju Yeon Shin, Yu Sung Chun, Hyeong Bin Jang, Choong Eui Song and Sang-gi Lee
    Accounts of Chemical Research2010 43 (7), 985-994

    Over the past decade, ionic liquids have received a great deal of attention as a new means for catalyst immobilization. Large numbers of catalysts having polar or ionic character have been successfully immobilized in ionic liquids, thus allowing their ...

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

  Nucleophilic Fluorination of Triflates by Tetrabutylammonium Bifluoride

  Kyu-Young Kim, Bong Chan Kim, Hee Bong Lee and Hyunik Shin
  The Journal of Organic Chemistry2008 73 (20), 8106-8108

  • Nucleophilic Fluorination of Triflates by Tetrabutylammonium Bifluoride

    Kyu-Young Kim, Bong Chan Kim, Hee Bong Lee and Hyunik Shin
    The Journal of Organic Chemistry2008 73 (20), 8106-8108
    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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