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Aminosulfur Trifluoride Deoxofluorination

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Fluorination

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

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Introduction

N,N-Dialkylaminosulfur trifluorides are very popular and useful deoxofluorination reagents [1]. N,N-Dimethylaminosulfur trifluoride as the first representative of this group was reported in 1964 [2], and N,N-diethylaminosulfur trifluoride called as DAST (b.p. 30–32 °C/3 mmHg) was prepared in 1970 [3]. The reaction of N,N-dialkylaminotrimethylsilanes with SF4, by which N,N-dimethylaminosulfur trifluoride and DAST were first prepared, has been still used as the main method for the syntheses of this group of compounds (Eq. 1) [1].

(1)

DAST underwent rapid decomposition (potentially explosive and detonation) with gas evolution when heating to over 90 °C [4]. In 1999, N,N-bis(2-methoxyethyl)aminosulfur trifluoride (Deoxo-Fluor or BAST) as a less thermally sensitive deoxofluorination reagent (b.p. 60 °C, 0.1 mmHg) was reported [5]. Although it was of similar reactivity to DAST for most of deoxofluorination reactions, Deoxo-Fluor was useful for the high temperature...

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Authors and Affiliations

  1. Department of Chemistry, School of Science, Xi’an Key Laboratory of Sustainable Energy Material Chemistry, and MOE Key Laboratory for Nonequilibrium Synthesis and Modulation of Condensed Matter, Xi’an Jiaotong University, Xi’an, China

    Mingyou Hu

  2. 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

    Mingyou Hu & Jinbo Hu

Authors
  1. Mingyou Hu
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  2. Jinbo Hu
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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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Hu, M., Hu, J. (2020). Aminosulfur Trifluoride Deoxofluorination. In: Hu, J., Umemoto, T. (eds) Fluorination. Synthetic Organofluorine Chemistry. Springer, Singapore. https://doi.org/10.1007/978-981-10-1855-8_55-1

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  • DOI: https://doi.org/10.1007/978-981-10-1855-8_55-1

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  • Print ISBN: 978-981-10-1855-8

  • Online ISBN: 978-981-10-1855-8

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