118235-42-0Relevant articles and documents
Perfluoroalkanesulfonylation of Alkynyl(phenyl)iodonium Tosylates by the Weakly Nucleophilic Sodium Perfluoroalkanesulfinates
Han, Jia-Bin,Yang, Lian,Chen, Xing,Zha, Gao-Feng,Zhang, Cheng-Pan
supporting information, p. 4119 - 4124 (2016/12/30)
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). (Figure presented.).
