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Fluorination pp 1–7Cite as

Fluorophosphorane Deoxofluorination

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

Introduction

Because of the unique properties of fluorine and C-F bond, incorporation of fluorine into organic molecules can often change their chemical, physical, and biological properties. Therefore, a number of applications of organofluorine compounds have been found in medicinals, agrochemicals, functional materials, and other fields [1,2,3,4]. The fluorine effect has been widely used in lipophilicity tuning, pKa modulation, and selective blocking of oxidative metabolism [3, 5]. Due to easy availability of alcohols, many efforts have been devoted to the development of reagents and reactions for converting alcohols to fluorinated compounds [6,7,8,9,10,11,12,13,14,15,16,17]. As early as the 1960s, several phosphine-based deoxofluorinating reagents were developed. This chapter summarizes synthesis and application of the phosphine-based reagents, difluoro(triphenyl)phosphorane (Ph3PF2), trifluoro(diphenyl)phosphorane (Ph2PF3), and tetrafluoro(phenyl)phosphorane (PhPF4) [18,19,20,21,22,

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Authors and Affiliations

  1. The Institute For Advanced Studies, Wuhan University, Wuhan, China

    Zhaoliang Yang & Xiao Shen

Authors
  1. Zhaoliang Yang
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  2. Xiao Shen
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Correspondence to Xiao Shen .

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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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Yang, Z., Shen, X. (2018). Fluorophosphorane Deoxofluorination. In: Hu, J., Umemoto, T. (eds) Fluorination. Synthetic Organofluorine Chemistry. Springer, Singapore. https://doi.org/10.1007/978-981-10-1855-8_45-1

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  • DOI: https://doi.org/10.1007/978-981-10-1855-8_45-1

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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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