Fluorination

Living Edition
| Editors: Jinbo Hu, Teruo Umemoto

Et3N·3HF Complex Fluorination for Preparing Alkyl Fluorides

  • Günter HaufeEmail author
Living reference work entry
DOI: https://doi.org/10.1007/978-981-10-1855-8_26-1

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...

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Authors and Affiliations

  1. 1.Organic Chemistry InstituteUniversity of MünsterMünsterGermany