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Journal Article

A Unified Strategy for Arylsulfur(VI) Fluorides from Aryl Halides: Access to Ar‐SOF3 Compounds

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Wang,  Lin
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Cornella,  Josep
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Wang, L., & Cornella, J. (2020). A Unified Strategy for Arylsulfur(VI) Fluorides from Aryl Halides: Access to Ar‐SOF3 Compounds. Angewandte Chemie International Edition, 59(52), 23510-23515. doi:10.1002/anie.202009699.


Cite as: https://hdl.handle.net/21.11116/0000-0007-A928-E
Abstract
A convenient protocol to selectively access various arylsulfur(VI) fluorides from commercially available aryl halides in a divergent fashion is presented. Firstly, a novel sulfenylation reaction with the electrophilic N‐(chlorothio)phthalimide (Cl‐S‐Phth) and arylzinc reagents afforded the corresponding Ar‐S‐Phth compounds. Subsequently, the S(II) atom was selectively oxidized to distinct fluorinated sulfur(VI) compounds under mild conditions. Slight modifications on the oxidation protocol permit the chemoselective installation of 1, 3, or 4 fluorine atoms at the S(VI) center, affording the corresponding Ar‐SO2F, Ar‐SOF3, and Ar‐SF4Cl. Of notice, this strategy enables the effective introduction of the rare and underexplored ‐SOF3 moiety into various (hetero)aryl groups. Reactivity studies demonstrate that such elusive Ar‐SOF3 can be utilized as a linchpin for the synthesis of highly coveted aryl sulfonimidoyl fluorides (Ar‐SO(NR)F).