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NFSI and Its Analogs Fluorination for Preparing Alkenyl Fluorides

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Fluorination

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

Introduction

The preparation of various N-fluorosulfonamides was first reported by Barton (Scheme 1) [1]. These compounds provided important precedent toward developing N-fluorobenzenesulfonimide (NFSI), due to their stability and synthesis from readily available precursors. Nevertheless, the potential to fluorinate carbanions was not explored until seminal work by Barnette that demonstrated the applicability of the reagents toward preparing fluorinated alkanes (Scheme 1b) [2]. Subsequently, Schwartz et al. pioneered an analogous transformation providing fluorinated alkenes (Scheme 1c) [3]. At that time, the reactions of alkenyl-metal (Hg, Al, B, and Zr) species with electrophilic halogen reagents were used to prepare vinyl halides, but the reactions had not been extended to fluorinated alkenes. To expand the scope of these transformations, Schwartz and coworkers used vinyl iodides as precursors to organolithium intermediates and demonstrated the stereospecific synthesis of...

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References

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Authors and Affiliations

  1. Department of Medicinal Chemistry, The University of Kansas, 4046A Malott Hall, 1251 Wescoe Hall Drive, Lawrence, KS, 66045, USA

    Francisco de Azambuja & Ryan A. Altman

Authors
  1. Francisco de Azambuja
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  2. Ryan A. Altman
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Corresponding author

Correspondence to Ryan A. Altman .

Editor information

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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de Azambuja, F., Altman, R.A. (2018). NFSI and Its Analogs Fluorination for Preparing Alkenyl Fluorides. In: Hu, J., Umemoto, T. (eds) Fluorination. Synthetic Organofluorine Chemistry. Springer, Singapore. https://doi.org/10.1007/978-981-10-1855-8_20-1

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  • DOI: https://doi.org/10.1007/978-981-10-1855-8_20-1

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  • Print ISBN: 978-981-10-1855-8

  • Online ISBN: 978-981-10-1855-8

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