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BF3 Fluorination for Preparing Alkyl Fluorides

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Fluorination

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

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Introduction

Monofluorination is an important access to introduce fluorine atom into organic molecules, which is realized by the strategies employing diethylaminosulfur trifluoride (DAST), tris(diethylamino)sulfonium difluorotrimethylsilicate (TAS-F), hydrogen fluoride, etc. as reagents as shown in other entries of the book. BF3.OEt2 as an ubiquitous reagent is usually used as a Lewis acid in synthetic organic transformations. However, BF3·OEt2 may also serve as an effective nucleophilic fluoride source in the fluorination reaction owing to the property of boron to form ate complex with some Lewis bases and anions. The mechanism of BF3 for fluoride transfer possibly involves a migration of the fluoride via an ate complex readily generated, trifluoroborate with the form of BF3X− (X = Lewis base). Because of its high fluoride content and easy handling in the reaction, the use of BF3·OEt2as a fluorine source has attracted great attention of synthetic chemists. A comprehensive review has...

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Authors and Affiliations

  1. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, China

    Chang-Hua Ding & Xue-Long Hou

Authors
  1. Chang-Hua Ding
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  2. Xue-Long Hou
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Correspondence to Chang-Hua Ding or Xue-Long Hou .

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Editors and Affiliations

  1. Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, China

    Jinbo Hu

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

    Teruo Umemoto

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Ding, CH., Hou, XL. (2020). BF3 Fluorination for Preparing Alkyl Fluorides. In: Hu, J., Umemoto, T. (eds) Fluorination. Synthetic Organofluorine Chemistry. Springer, Singapore. https://doi.org/10.1007/978-981-10-3896-9_43

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