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| Editors: Jinbo Hu, Teruo Umemoto

N,N-Dialkylaminosulfur Trifluoride Dethiofluorination

  • Mingyou Hu
  • Jinbo HuEmail author
Living reference work entry
DOI: https://doi.org/10.1007/978-981-10-1855-8_56-1


N,N-Dialkylaminosulfur trifluorides are useful not only as deoxofluorination reagents but also as dethiofluorination reagents. Thus, the dialkylaminosulfur trifluorides reacted with organosulfur compounds such as thioesters, thioketones, etc. to give the corresponding dethiofluorinated compounds [1, 2]. On the other hand, a similar sulfur-mediated fluorination methodology was successfully applied to synthesize glycosyl fluorides, which were very useful synthetic intermediates in oligosaccharide chemistry [3, 4, 5, 6, 7, 8, 9].

Dethiofluorination of Thioesters, Thioketones, and Related Thio Compounds with DAST or Deoxofluor

In 1990, it was reported that thioesters reacted with N,N-diethylaminosulfur trifluorides (DAST) under mild conditions to give the corresponding difluoro ethers in high yields as shown in Eqs. ( 1) and ( 2) [ 1]. This is a useful method because esters themselves could not react with a dialkylaminosulfur trifluoride.
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© Springer Nature Singapore Pte Ltd. 2020

Authors and Affiliations

  1. 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 MatterXi’an Jiaotong UniversityXi’anChina
  2. 2.Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular SynthesisShanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of SciencesShanghaiChina