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

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.

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Genre: Journal Article

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 Creators:
Wang, Lin1, Author              
Cornella, Josep1, Author              
Affiliations:
1Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2466693              

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Free keywords: heterocycles; sulfinyl trifluorides; sulfonimidoyl fluorides; sulfonyl fluorides; tetrafluorosulfanyl chlorides
 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).

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Language(s): eng - English
 Dates: 2020-07-142020-09-172020-12-21
 Publication Status: Published in print
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.202009699
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 59 (52) Sequence Number: - Start / End Page: 23510 - 23515 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851