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

Sandip S. Shinde, Byoung Se Lee and Dae Yoon Chi*

*Department of Chemistry, Sogang University, 1 Shinsudong, Mapoku, Seoul 121-742, Korea, Email: dychisogang.ac.kr

S. S. Shinde, B. S. Lee, D. Y. Chi, Org. Lett., 2008, 10, 733-735.

DOI: 10.1021/ol702679d (free Supporting Information)


Abstract

A synergistic effect in nucleophilic fluorination has been demonstrated for the molecular combination of an ionic liquid and a tert-alcohol. Consequently, these functionalized ILs not only increase the nucleophilic reactivities of the fluoride anion but also remarkably reduce the olefin byproduct.

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Significantly Enhanced Reactivities of the Nucleophilic Substitution Reactions in Ionic Liquid

D. W. Kim, C. E. Song, D. Y. Chi, J. Org. Chem., 2003, 68, 4281-4285.


Key Words

Fluorination, Finkelstein Reaction, Ionic Liquids


ID: J54-Y2008-0550