Perfluoroalkanesulfonylation of Alkynyl(phenyl)iodonium Tosylates by the Weakly Nucleophilic Sodium Perfluoroalkanesulfinates. Issue 24 (25th November 2016)

• Record Type: Journal Article
• Authors: Han, Jia‐Bin; Yang, Lian; Chen, Xing; Zha, Gao‐Feng; Zhang, Cheng‐Pan
• Is Part Of: Advanced synthesis & catalysis. Volume 358:Issue 24(2016)
• Page Start: 4119
• Page End: 4124
• Publication Date: 2016-11-25
• Subjects: alkynes -- fluorine -- iodonium salts -- perfluoroalkanesulfonylation -- substituent effects -- transition metal-free conditions; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201600717
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: An additive‐ and transition metal‐free perfluoroalkanesulfonylation of alkynyl(phenyl)iodonium tosylates with sodium perfluoroalkanesulfinates (Rfn SO2 Na) is described. The poorly nucleophilic Rfn SO2 Na 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 (Rfn SO2 Na). Abstract :