English
 
User Manual Privacy Policy Disclaimer Contact us
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT

Released

Journal Article

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

MPS-Authors
/persons/resource/persons252493

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

/persons/resource/persons207433

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

External Ressource
No external resources are shared
Fulltext (public)
There are no public fulltexts stored in PuRe
Supplementary Material (public)
There is no public supplementary material available
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: http://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).