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Fluorination pp 1–32Cite as

Hypervalent Iodine Fluorination for Preparing Alkyl Fluorides (Stoichiometrically and Catalytically)

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

Introduction

Fluorinated hypervalent iodine (III) reagents are a century-old class of compounds undergoing a resurgence over the past few decades. The renewed interest in these compounds stems from their ability to transfer fluorine to Lewis basic reagents as though they were a source of fluoronium “F+” ion. The purpose of this chapter is to introduce the reader to this growing field of fluorination chemistry by illustrating key trends and reactivity patterns, from the first synthesis of the reagent to the most recent advancements in catalytic asymmetric fluorinations [1]. The discussion will follow the chemistry of two classes of fluorinated hypervalent iodine (III) compounds, the (difluoroiodo)arenes (1) and the fluorinated iodobenzoxole (2) (Fig. 1). While this is intended to be comprehensive, the focus will be on discussing the differing reactivity patterns induced by these compounds, as opposed to presenting an exhaustive list of all the work.

Fig. 1
figure 1

Structures of commonly...

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Author information

Authors and Affiliations

  1. Department of Chemistry, University of Waterloo, Waterloo, ON, Canada

    Graham K. Murphy

  2. Department of Chemistry and Catalysis Research Center (CRC), Technical University Munich, Garching, Germany

    Tanja Gulder

Authors
  1. Graham K. Murphy
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  2. Tanja Gulder
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Corresponding authors

Correspondence to Graham K. Murphy or Tanja Gulder .

Editor information

Editors and Affiliations

  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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Murphy, G.K., Gulder, T. (2018). Hypervalent Iodine Fluorination for Preparing Alkyl Fluorides (Stoichiometrically and Catalytically). In: Hu, J., Umemoto, T. (eds) Fluorination. Synthetic Organofluorine Chemistry. Springer, Singapore. https://doi.org/10.1007/978-981-10-1855-8_39-1

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  • DOI: https://doi.org/10.1007/978-981-10-1855-8_39-1

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  • Publisher Name: Springer, Singapore

  • Print ISBN: 978-981-10-1855-8

  • Online ISBN: 978-981-10-1855-8

  • eBook Packages: Springer Reference Chemistry and Mat. ScienceReference Module Physical and Materials ScienceReference Module Chemistry, Materials and Physics

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