Synthesis of Highly Reactive Sulfone Iminium Fluorides and Their Use in Deoxyfluorination and Sulfur Fluoride Exchange Chemistry

We report the synthesis of sulfone iminium fluorides (SIFs), a reactive class of sulfur­(VI) molecules. The synthesis is tolerant of a variety of substituents on the sulfur and nitrogen components. The SIF reagents were applied to the deoxyfluorination of alcohols and carboxylic acids, providing hig...

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Published inOrganic letters Vol. 24; no. 32; pp. 5962 - 5966
Main Authors Vogel, James A., Hammami, Rania, Ko, Ara, Datta, Hiya, Eiben, Yael N., Labenne, Karley J., McCarver, Ellis C., Yilmaz, Ebrar Z., Melvin, Patrick R.
Format Journal Article
LanguageEnglish
Published American Chemical Society 19.08.2022
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Summary:We report the synthesis of sulfone iminium fluorides (SIFs), a reactive class of sulfur­(VI) molecules. The synthesis is tolerant of a variety of substituents on the sulfur and nitrogen components. The SIF reagents were applied to the deoxyfluorination of alcohols and carboxylic acids, providing high yields of fluorinated products in 60 s at room temperature. The SIF reagents were then utilized in sulfur fluoride exchange (SuFEx), creating the first ionic SuFEx products to date.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c02232