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TBAF Fluorination for Preparing Alkyl Fluorides

Fluorination

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

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Introduction

Fluorinated alkyl substituents appear widely in medicinal and pharmaceutical chemistry [1,2,3,4,5,6,7], and [18F]-fluorinated ethyl or propyl tags are increasingly common tools radiochemists use to prepare [18F]-labeled radiopharmaceuticals for positron emission tomography (PET) [8,9,10,11]. Numerous fluorinating reagents that are available to prepare alkyl fluorides through nucleophilic, electrophilic, and radical approaches are covered elsewhere in this volume. Here we will review fluorinations with the readily available and prototypical nucleophilic fluorinating reagent tetrabutylammonium fluoride (TBAF) and its derivatives.

In the gas phase, fluoride is an incredibly potent nucleophile and strong base because of its concentration of charge (as the smallest monoanion) and because of its propensity to form very strong bonds with hydrogen and carbon. In solution, the situation is quite different: strong ion pairing with cations, dipolar interactions with solvent...

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Author information

Authors and Affiliations

  1. Department of Chemistry, University of South Dakota, 414 E. Clark Street, Vermillion, SD, 57069, USA

    Haoran Sun

  2. Departments of Medicinal Chemistry & Pharmacognosy and Chemistry, College of Pharmacy, University of Illinois at Chicago, 1200 West Harrison St, Chicago, IL, 60612, USA

    Stephen G. Dimagno

Authors
  1. Haoran Sun
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  2. Stephen G. Dimagno
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Correspondence to Haoran Sun .

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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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Sun, H., Dimagno, S.G. (2018). TBAF Fluorination for Preparing Alkyl Fluorides. In: Hu, J., Umemoto, T. (eds) Fluorination. Synthetic Organofluorine Chemistry. Springer, Singapore. https://doi.org/10.1007/978-981-10-1855-8_14-1

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  • DOI: https://doi.org/10.1007/978-981-10-1855-8_14-1

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  • Print ISBN: 978-981-10-1855-8

  • Online ISBN: 978-981-10-1855-8

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  1. Latest

    TBAF Fluorination for Preparing Alkyl Fluorides
    Published:
    23 January 2018

    DOI: https://doi.org/10.1007/978-981-10-1855-8_14-2

  2. Original

    TBAF Fluorination for Preparing Alkyl Fluorides
    Published:
    28 September 2017

    DOI: https://doi.org/10.1007/978-981-10-1855-8_14-1

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