Unbalanced-Ion-Pair-Catalyzed Nucleophilic Fluorination Using Potassium Fluoride.
作者信息
Li Wangbing, Lu Zhichao, Hammond Gerald B, Xu Bo
机构信息
Key Laboratory of Science and Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai, 201620, China.
Department of Chemistry, University of Louisville, Louisville, Kentucky 40292, United States.
出版信息
Org Lett. 2021 Dec 17;23(24):9640-9644. doi: 10.1021/acs.orglett.1c03887. Epub 2021 Dec 1.
An unbalanced ion pair promoter (e.g., tetrabutylammonium sulfate), consisting of a bulky and charge-delocalized cation and a small and charge-localized anion, greatly accelerates nucleophilic fluorinations using easy handling KF. We also successfully converted an inexpensive and commercially available ion-exchange resin to the polymer-supported ion pair promoter (A26-SO), which could be reused after filtration. Moreover, A26-SO can be used in continuous flow conditions. In our conditions, water is well-tolerated.
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