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Et3N·3HF Complex Fluorination for Preparing Alkyl Fluorides

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Fluorination

Part of the book series: Synthetic Organofluorine Chemistry ((SYOC))

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Introduction

Fluorinated organic compounds, both analogues of natural products and synthetic materials, gain enormous interest by organic and medicinal chemists, biochemists, material scientists, and others because of its unique chemical properties and biological activity. Consequently, there is a continuously growing demand of methods to synthesize such compounds. Although plenty of methods to introduce fluorine and fluorinated groups into organic compounds do exist, not all used reagents can be handled easily and safely in ordinary organic chemistry laboratories. A frequently used fluorination reagent is the triethylamine trihydrofluoride complex, Et3N·3HF [triethylamine tris(hydrogenfluoride)] as a source of nucleophilic fluoride [1,2,3,4].

Originally, Et3N·3HF was formed in situ for ring opening of epoxides [5]. In 1980, Franz prepared the neat reagent by addition of an ethereal solution of anhydrous HF to a slight excess of Et3N at 0 °C, followed by distillation of the separated...

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  1. Organic Chemistry Institute, University of Münster, Münster, Germany

    Günter Haufe

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  1. Günter Haufe
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  1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, China

    Jinbo Hu

  2. R&D Center, Zhejiang Jiuzhou Pharmaceutical Co., Ltd, Taizhou, Zhejiang, China

    Teruo Umemoto

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Haufe, G. (2019). Et3N·3HF Complex Fluorination for Preparing Alkyl Fluorides. In: Hu, J., Umemoto, T. (eds) Fluorination. Synthetic Organofluorine Chemistry. Springer, Singapore. https://doi.org/10.1007/978-981-10-1855-8_26-1

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