Fluorination

Living Edition
| Editors: Jinbo Hu, Teruo Umemoto

N,N′-Difluoro-1,4-Diazoniabicyclo[2.2.2]octane Salt Electrophilic Fluorination

  • Chaohuang Chen
  • Pinhong Chen
  • Guosheng LiuEmail author
Living reference work entry
DOI: https://doi.org/10.1007/978-981-10-1855-8_47-1

Introduction

Electrophilic fluorination reaction has been proven to be a straightforward strategy for the incorporation of fluorine into molecules. Hence, the development of effective electrophilic fluorinating reagents is important [ 1]. Gratefully, by direct fluorination of N-substituted 1,4-diazabicyclo[2.2.2]octane (DABCO) salts or DABCO itself, a series of DABCO-based electrophilic fluorinating reagents ( 1–6) were synthesized and used as fluorine donors or oxidants (Fig. 1) [ 1, 2]. Among them, the commercially available Selectfluor TM reagent ( 2) has been widely studied and applied to the organic synthesis due to its high reactivity and ready availability [ 3]. Meanwhile, other structurally similar reagents such as l-alkyl-4-fluoro-l,4-diazoniabicyclo[2.2.2]octane salts ( 3, alkyl = CH 2CF 3 [ 4]; 4, alkyl = CH 2CN [ 5]), 1,4-difluoro-1,4-diazoniabicyclo[2.2.2]octane salts [ 6] ( 5), and 1-hydroxy-1,4-diazoniabicyclo[2.2.2]octane salts [ 7] ( 6) were far less developed.
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© Springer Nature Singapore Pte Ltd. 2019

Authors and Affiliations

  1. 1.State Key Laboratory of Organometallic ChemistryShanghai Institute of Organic Chemistry, Chinese Academy of SciencesShanghaiChina