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Synfacts 2019; 15(08): 0909
DOI: 10.1055/s-0039-1690113
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Ion-Exchange-Resin-Supported Hydrogen Fluoride for Fluorination Reactions

Contributor(s):
Yasuhiro Uozumi
,
Anggi Eka Putra
Lu Z, Bajwa BS, Otome OE, Hammond GB. * Xu B. * University of Louisville and California State University, Fresno, USA; Donghua University, Shanghai, P. R. of China
Multifaceted Ion Exchange Resin-Supported Hydrogen Fluoride: A Path to Flow Hydrofluorination.

Green Chem. 2019;
21: 2224-2228
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Further Information

Publication History

Publication Date:
18 July 2019 (online)

 
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Key words

hydrogen fluoride - fluorination - flow reaction - hydrofluorination - ion-exchange resin

Significance

A solid anhydrous hydrogen fluoride-equivalent reagent (A26-HF) was prepared by treatment of ion-exchange resin with HF gas (eq. 1). A26-HF was used as a source of HF in the hydrofluorination of alkenes (eq. 2), the ring-opening fluorination of aziridines (eq. 3), and a fluoro-Prins reaction (eq. 4) to give a variety of fluorinated products in up to 89% yield.


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Comment

The ion-exchange-resin-supported hydrogen fluoride was applied to the flow hydrofluorination of 3-methylbut-3-en-1-yl benzoate to give 3-fluoro-3-methylbutyl benzoate in 92% NMR yield. In a thermostability test, only a 2 wt% loss of HF was detected when A26-HF was exposed to air at room temperature for 30 hours.


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