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

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-SO₂ F, Ar-SOF₃ , and Ar-SF₄ Cl. 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).

SUBMITTER: Wang L

PROVIDER: S-EPMC7756513 | biostudies-literature | 2020 Dec

REPOSITORIES: biostudies-literature

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

Wang Lin L Cornella Josep J

Angewandte Chemie (International ed. in English) 20201026 52

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 permi ...[more]

PMID: 32940381

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