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N-Haloimide/HF Dethiofluorination

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Fluorination

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

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Introduction

Synthetic methods for organofluorine compounds[1] are categorized roughly into two types [2]: (1) fluorination and (2) use of fluorinated building blocks. Fluorination is further classified into three classes depending on the nature of fluorinating species: (1) electrophilic fluorination (from C-H to C-F using F2 or electrophilic agents), (2) nucleophilic fluorination (from C-Lv (Lv: leaving group) to C-F using fluoride reagents), and (3) deoxofluorination (replacement of hydroxyl or carbonyl groups with one or two fluorides, respectively).

Nucleophilic fluorination is the most accessible reaction, since fluoride ion reagents are stable and easy to handle. However, a fluoride ion is a hard base and poor nucleophile, although bifluoride F- (HF) (or HF2-) and dihydrogen trifluoride F- (HF)2 (or H2F3-) are deemed better nucleophiles. Accordingly, a reactive enough leaving group is essential for successful nucleophilic fluorination. Halogens (Cl, Br, and I), tosylates, and/or...

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Author information

Authors and Affiliations

  1. Department of Applied Chemistry, Faculty of Engineering, Okayama University, Okayama, Japan

    Manabu Kuroboshi

  2. Research and Development Initiative, Chuo University, Bunkyo-ku, Tokyo, Japan

    Tamejiro Hiyama

Authors
  1. Manabu Kuroboshi
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  2. Tamejiro Hiyama
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Corresponding author

Correspondence to Manabu Kuroboshi .

Editor information

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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Kuroboshi, M., Hiyama, T. (2020). N-Haloimide/HF Dethiofluorination. In: Hu, J., Umemoto, T. (eds) Fluorination. Synthetic Organofluorine Chemistry. Springer, Singapore. https://doi.org/10.1007/978-981-10-3896-9_3

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