Perfluoroalkanesulfonylation of Alkynyl(phenyl)iodonium Tosylates by the Weakly Nucleophilic Sodium Perfluoroalkanesulfinates
| Autor: | Jia-Bin Han, Xing Chen, Gao-Feng Zha, Lian Yang, Cheng-Pan Zhang |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
010405 organic chemistry
Sodium Nitrogen atmosphere chemistry.chemical_element General Chemistry 010402 general chemistry 01 natural sciences Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound Nucleophile chemistry Reagent Fluorine Moiety Organic chemistry Carbene Dichloromethane |
| Zdroj: | Advanced Synthesis & Catalysis. 358:4119-4124 |
| ISSN: | 1615-4150 |
| DOI: | 10.1002/adsc.201600717 |
| Popis: | An additive- and transition metal-free perfluoroalkanesulfonylation of alkynyl(phenyl)iodonium tosylates with sodium perfluoroalkanesulfinates (RfnSO2Na) is described. The poorly nucleophilic RfnSO2Na reacted with alkynyl(phenyl)iodonium salts in dichloromethane at room temperature under a nitrogen atmosphere for 5–60 minutes to afford a variety of acetylenic triflones and alkynyl perfluoroalkyl sulfones in good to quantitative yields. The position of substituents on the phenyl rings of the arylethynyl moiety in the iodonium salts had a big influence on the reaction. The formation of five-membered cyclic vinyl sulfones suggested that the reaction proceeds via an alkylidene carbene intermediate. Furthermore, successful scaling-up of the reaction demonstrates the practicality of the new method. Advantages of the method include short reaction times, mild conditions, and the easy access to perfluoroalkanesulfonylation reagents (RfnSO2Na). |
| Databáze: | OpenAIRE |
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