Radical-mediated vicinal addition of alkoxysulfonyl/fluorosulfonyl and trifluoromethyl groups to aryl alkyl alkynes. Issue 35 (9th August 2021)

• Record Type: Journal Article
• Authors: Dong, Xinrui; Jiang, Wenhua; Hua, Dexiang; Wang, Xiaohui; Xu, Liang; Wu, Xiaoxing
• Is Part Of: Chemical science. Volume 12:Issue 35(2021)
• Page Start: 11762
• Page End: 11768
• Publication Date: 2021-08-09
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d1sc03315h
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : An unprecedented method for vicinal addition of alkoxysulfonyl/fluorosulfonyl and trifluoromethyl groups to aryl alkyl alkynes has been developed to afford useful alkenylsulfonate esters and alkenylsulfonyl fluorides. Abstract : The addition of sulfonyl radicals to alkenes and alkynes is a valuable method for constructing useful highly functionalized sulfonyl compounds. The underexplored alkoxy- and fluorosulfonyl radicals are easily accessed by CF3 radical addition to readily available allylsulfonic acid derivatives and then β-fragmentation. These substituted sulfonyl radicals add to aryl alkyl alkynes to give vinyl radicals that are trapped by trifluoromethyl transfer to provide tetra-substituted alkenes bearing the privileged alkoxy- or fluorosulfonyl group on one carbon and a trifluoromethyl group on the other. This process exhibits broad functional group compatibility and allows for the late-stage functionalization of drug molecules, demonstrating its potential in drug discovery and chemical biology.