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Pyrene-Tagged Ionic Liquids: Separable Organic Catalysts for SN2 Fluorination

Abu Taher, Kyo Chul Lee, Hye Ji Han and Dong Wook Kim*

*Department of Chemistry and Chemical Engineering, Inha University, 100 Inha-ro, Nam-gu, Incheon 402-751, Korea, Email: kimdwinha.ac.kr

A. Taher, K. C. Lee, H. J. Han, D. W. Kim, Org. Lett., 2017, 19, 3342-3345.

DOI: 10.1021/acs.orglett.7b01064 (free Supporting Information)


Abstract

A pyrene-substituted imidazolium-based ionic liquid (PIL) serves as organic catalyst for the SN2 fluorination using CsF. In this system, the PIL significantly enhanced the reactivity of the metal fluoride due to the phase-transfer catalytic effect of the imidazolium moiety as well as the metal cation-π (pyrene) interactions. Furthermore, PIL can easily be separated from the reaction mixture using reduced graphene oxide by π-π stacking.

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Concept of pyrene-tagged ionic liquids as multifunctional organic catalysts



Key Words

Finkelstein Reaction, Alkyl Fluorides, Ionic Liquids, Organocatalysis


ID: J54-Y2017