Synthesis of 1,2-Bis(trifluoromethylthio)arenes via Aryne Intermediates

Synthesis of 1,2-Bis(trifluoromethylthio)arenes via Aryne Intermediates

A general method for synthesis of 1,2-bis-trifluoro­methyl­thioarenes has been developed. Arynes generated from silyl aryl triflates or halides react with bis­(trifluoro­methyl)­disulfide to afford 1,2-bis-trifluoro­methyl­thioarenes. Aryl, alkyl, ester, halide, and methoxy functionalities are compa...

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Veröffentlicht in:Organic letters 2017-08, Vol.19 (16), p.4247-4250
Hauptverfasser: Mesgar, Milad, Daugulis, Olafs
Format: Artikel
Sprache:eng
Schlagworte:
aromatic hydrocarbons
chemical reactions
chemical structure
Chemistry Techniques, Synthetic
Cyclization
Fused-Ring Compounds - chemical synthesis
halides
Molecular Structure
Spiro Compounds - chemical synthesis
Structure-Activity Relationship
sulfides
Sulfides - chemical synthesis
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Zusammenfassung:A general method for synthesis of 1,2-bis-trifluoro­methyl­thioarenes has been developed. Arynes generated from silyl aryl triflates or halides react with bis­(trifluoro­methyl)­disulfide to afford 1,2-bis-trifluoro­methyl­thioarenes. Aryl, alkyl, ester, halide, and methoxy functionalities are compatible with reaction conditions. Use of bis­(perfluoroaryl)­disulfides gave moderate yields of aryne disulfenylation or cyclization to fluorinated dibenzothiophenes.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.7b01901