Unbalanced-Ion-Pair-Catalyzed Nucleophilic Fluorination Using Potassium Fluoride

Wangbing Li; Zhichao Lu; Gerald B Hammond; Bo Xu

doi:10.1021/acs.orglett.1c03887

Unbalanced-Ion-Pair-Catalyzed Nucleophilic Fluorination Using Potassium Fluoride

Org Lett. 2021 Dec 17;23(24):9640-9644. doi: 10.1021/acs.orglett.1c03887. Epub 2021 Dec 1.

Authors

Wangbing Li¹, Zhichao Lu², Gerald B Hammond², Bo Xu¹

Affiliations

¹ Key Laboratory of Science and Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai, 201620, China.
² Department of Chemistry, University of Louisville, Louisville, Kentucky 40292, United States.

PMID: 34851641
DOI: 10.1021/acs.orglett.1c03887

Abstract

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-SO₄^2-), which could be reused after filtration. Moreover, A26-SO₄^2- can be used in continuous flow conditions. In our conditions, water is well-tolerated.