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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:

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

DOI: 10.1021/ol702679d (free Supporting Information)


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.

see article for more examples

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