Introduction
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.
In 2000, bis(methoxyethyl)aminosulfur...
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References
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Hu, M., Hu, J. (2020). N,N-Dialkylaminosulfur Trifluoride Dethiofluorination. In: Hu, J., Umemoto, T. (eds) Fluorination. Synthetic Organofluorine Chemistry. Springer, Singapore. https://doi.org/10.1007/978-981-10-1855-8_56-1
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DOI: https://doi.org/10.1007/978-981-10-1855-8_56-1
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