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2,2-Difluoro-1,3-Dimethylimidazolidine (DFI) Deoxofluorination

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Fluorination

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

Introduction

2,2-Difluoro-1,3-dimethylimidazolidine (DFI) was first reported as a novel deoxofluorination reagent by Hayashi and coworkers in 2002 [1]. It is a clear liquid with boiling point of 47 Â°C at 37 mmHg and melting point of −8.7 Â°C [1]. In terms of the chemical structure, DFI is similar to other α,α-difluoroalkylamine agents such as Yarovenko [2] and Ishikawa [3] agent. Accelerating rate calorimetry (ARC) analysis showed that thermal decomposition of DFI begins at 150 Â°C [1], while diethylaminosulfur trifluoride (DAST) decomposes at about 90 Â°C [4], indicating that DFI is much more thermally stable.

Deoxofluorination with DFI

DFI is more reactive than Yarovenko and Ishikawa agents due to the stabilizing effects endowed by the two nitrogen atoms adjacent to difluoromethylene. In addition to alcohols and carboxylic acids, aldehydes/ketones and even some phenols can be converted to the corresponding deoxofluorinated products. The reaction can be performed in acetonitrile,...

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References

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Authors 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

    Lingchun Li & Jinbo Hu

Authors
  1. Lingchun Li
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  2. Jinbo Hu
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Corresponding author

Correspondence to Jinbo Hu .

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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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Li, L., Hu, J. (2019). 2,2-Difluoro-1,3-Dimethylimidazolidine (DFI) Deoxofluorination. In: Hu, J., Umemoto, T. (eds) Fluorination. Synthetic Organofluorine Chemistry. Springer, Singapore. https://doi.org/10.1007/978-981-10-1855-8_48-1

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  • DOI: https://doi.org/10.1007/978-981-10-1855-8_48-1

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  • Publisher Name: Springer, Singapore

  • Print ISBN: 978-981-10-1855-8

  • Online ISBN: 978-981-10-1855-8

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