Solvent-free synthesis of alkyl and fluoroalkyl sulfonium salts from sulfides and fluoroalkyl trifluoromethanesulfonates
| Autor: | Xiao-Yan Wang, Su-Jiao Jia, Hai-Xia Song, Shi-Meng Wang, Cheng-Pan Zhang, Jia-Bin Han, Gao Ying |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
chemistry.chemical_classification
Solvent free Sulfide 010405 organic chemistry Sulfonium Aryl Organic Chemistry 010402 general chemistry 01 natural sciences Biochemistry Medicinal chemistry 0104 chemical sciences Inorganic Chemistry chemistry.chemical_compound Reaction temperature chemistry Yield (chemistry) Environmental Chemistry Organic chemistry Physical and Theoretical Chemistry Alkyl |
| Zdroj: | Journal of Fluorine Chemistry. 192:131-140 |
| ISSN: | 0022-1139 |
| DOI: | 10.1016/j.jfluchem.2016.10.020 |
| Popis: | A series of diaryl(fluoroalkyl)sulfonium salts were synthesized from electron-rich diaryl sulfides and fluoroalkyl trifluoromethanesulfonates under solvent-free conditions. Unlike diaryl sulfides, dialkyl and alkyl(aryl) sulfides reacted with fluoroalkyl trifluoromethanesulfonates (e.g. CF3SO3CH2CF3, CF3SO3CH2CF2H) to provide trialkyl- and aryl(dialkyl)sulfonium trifluoromethanesulfonates in good yields, wherein dialkyl- and alkyl(aryl)(fluoroalkyl)sulfonium salts were formed, respectively, and nucleophilically attacked by a second sulfide to yield the non-fluorinated sulfoniums. The SN2-type reaction could stop at the first step and exclusively afford dialkyl- and alkyl(aryl)(fluoroalkyl)sulfonium salts, which was dramatically dependent upon the structure of sulfides, the nature of fluoroalkyl trifluoromethanesulfonates, the reactant ratio, and/or the reaction temperature. This protocol allows for an efficient and convenient access to a variety of alkyl and fluoroalkyl sulfonium salts. |
| Databáze: | OpenAIRE |
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