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Tetrafluoroborate Salt Fluorination for Preparing Alkyl Fluorides

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Fluorination

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

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Introduction

The tetrafluoroborate ion, BF4−, is often described as “inert,” “non-nucleophilic,” and a “spectator ion.” Whilst this holds true in many instances, there are in fact an ever-increasing number of synthetically-relevant examples of fluoride transfer from the BF4− ion to an electrophilic carbon atom resulting in formation of organic fluorides. Perhaps the best-recognised transformation of this type is the Balz-Schiemann reaction (production of aryl fluorides from the pyrolysis of aryldiazonium tetrafluoroborates), which was first reported 90 years ago [1]. The utility of tetrafluoroborate salts (as well as boron trifluoride) for organic fluoride synthesis was recently and comprehensively reviewed by us, including all reported examples up to the end of 2013 [2]. The present account aims to explicate to the reader the various tactics and pitfalls involved in those reactions which result in the preparation of alkyl fluorides (i.e., form a C(sp3)–F bond) in a synthetically...

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Authors and Affiliations

  1. Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Oxford, UK

    Stephen G. Davies & Paul M. Roberts

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  1. Stephen G. Davies
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  2. Paul M. Roberts
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Correspondence to Stephen G. Davies .

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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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Davies, S.G., Roberts, P.M. (2020). Tetrafluoroborate Salt 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_4

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