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A Unified Strategy for Arylsulfur(VI) Fluorides from Aryl Halides: Access to Ar‐SOF 3 Compounds
Author(s) -
Wang Lin,
Cornella Josep
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202009699
Subject(s) - chemistry , aryl , phthalimide , electrophile , moiety , reagent , halide , combinatorial chemistry , reactivity (psychology) , medicinal chemistry , organic chemistry , catalysis , medicine , alkyl , alternative medicine , pathology
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‐SO 2 F, Ar‐SOF 3 , and Ar‐SF 4 Cl. Of notice, this strategy enables the effective introduction of the rare and underexplored ‐SOF 3 moiety into various (hetero)aryl groups. Reactivity studies demonstrate that such elusive Ar‐SOF 3 can be utilized as a linchpin for the synthesis of highly coveted aryl sulfonimidoyl fluorides (Ar‐SO(NR)F).