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2020 | OriginalPaper | Chapter

Ar-SF₄Cl Deoxofluorination

Authors : Benqiang Cui, Norio Shibata

Published in: Fluorination

Publisher: Springer Singapore

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Eccentric properties of fluorine such as highest electronegativity and smallest atomic radius after the hydrogen atom make the fluorine atom a pivotal element in biological and material applications. A variety of methods now exist for introducing fluorine into organic molecules [1, 2, 6‐8, 11, 28‐30, 36, 43, 44]. Among them, deoxo- and dethioxo fluorination methods involving the direct replacement of oxygen and/or sulfur moieties in substrates with fluorine are one of the most effective approaches for the selective synthesis of organofluorine compounds. Various reagents such as SF₄ [14], DAST (diethylaminosulfur trifluoride) [26], Deoxo-Fluor [bis(2-methoxyethyl)aminosulfur trifluoride] [3], DFI (2,2-difluoro-1,3-dimethylimidazolidine) [15], DFMBA (N,N-diethyl-α,α-difluoro-m-methylbenzylamine) [22], TFFH (fluoro-N,N,N′,N′-tetramethylformamidinium hexafluorophosphate) [9], PhenoFluor [1,3-bis(2,6-diisopropylphenyl)-2,2-difluoro-2,3-dihydro-1H-imidazole] [38], CpFluors (3,3-difluoro-1,2-diarylcyclopropene) [27], XtalFluor-E [(diethylamino)difluorosulfonium tetrafluoroborate] and XtalFluor-M (difluoro-4-morpholinylsulfonium tetrafluoroborate) [3, 25], Fluolead (4-tert-butyl-2,6-dimethylphenylsulfur trifluoride) [42], and PyFluor (2-pyridinesulfonyl fluoride) [31] have been developed for this purpose. The title compounds, arylsulfur chlorotetrafluorides (ArSF₄Cl), fluorinate many kinds of oxy- and sulfur-containing substrates such as alcohols, aldehydes, ketones, diketones, carboxylic acids, and sulfur compounds to corresponding fluoro-compounds in the presence of reducing reagents. Arylsulfur trifluorides (ArSF₃) generated in situ from ArSF₄Cl are reactive species in this transformation. Sulfur substrates are directly fluorinated with ArSF₄Cl without the addition of reducing agents transferring to the corresponding fluorinated compounds (Fig. 1) [41]. …

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previous chapter Aminosulfur Trifluoride Deoxofluorination

next chapter Balz-Schiemann Reaction

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Title: Ar-SF4Cl Deoxofluorination
Authors: Benqiang Cui
Norio Shibata
Publisher: Springer Singapore
Book: Fluorination
Print ISBN: 978-981-10-3895-2

Electronic ISBN: 978-981-10-3896-9

Copyright Year: 2020
DOI: https://doi.org/10.1007/978-981-10-3896-9_18

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