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Fluorination of Diaryliodonium Salts for Preparing Aryl Fluorides

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Fluorination

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

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Introduction

Diaryliodonium salts are a class of hypervalent iodine (III) reagents that have been known since 1894 (Fig. 1) [14]. Although the term “salt” is commonly used, the T-shaped form shown by X-ray structures illustrates that these iodine (III) compounds have more covalent bond characteristics. “Diaryl-λ3-iodanes” is the nomenclature from IUPAC for this type of molecule [25, 36, 45, 46, 48]. Diaryliodonium salts with tetrafluoroborates, triflates, and tosylates as counter anions are frequently used due to their good solubility in general organic solvents, as well as the lack of nucleophilicity of these anions, compared with halide anion salts.

Fluorination of Diaryliodonium Salts for Preparing Aryl Fluorides, Fig. 1
figure 624 figure 624

General structure and T-shaped form of diaryliodonium salts

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Authors and Affiliations

  1. Citigroup of Biomedical Imaging Center, Weill Cornell Medicine, New York, NY, USA

    Wenchao Qu

  2. Department of Discovery, Avid Radiopharmaceuticals, Philadelphia, PA, USA

    Ximin Li

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  1. Wenchao Qu
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  2. Ximin Li
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Correspondence to Wenchao Qu or Ximin Li .

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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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Qu, W., Li, X. (2020). Fluorination of Diaryliodonium Salts for Preparing Aryl Fluorides. In: Hu, J., Umemoto, T. (eds) Fluorination. Synthetic Organofluorine Chemistry. Springer, Singapore. https://doi.org/10.1007/978-981-10-3896-9_12

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