Dearomatization of aryl sulfoxides: a switch between mono- and dual-difluoroalkylation. Issue 11 (27th February 2020)

• Record Type: Journal Article
• Authors: Huang, Xin; Zhang, Yage; Liang, Weijian; Zhang, Qifeng; Zhan, Yaling; Kong, Lichun; Peng, Bo
• Is Part Of: Chemical science. Volume 11:Issue 11(2020)
• Page Start: 3048
• Page End: 3053
• Publication Date: 2020-02-27
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d0sc00244e
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : Herein we describe the dearomatization of aryl sulfoxides with difluoroenol silyl ether (DFESE) using a rearrangement/addition protocol. Abstract : Herein we describe the dearomatization of aryl sulfoxides with difluoroenol silyl ether (DFESE) using a rearrangement/addition protocol. The selection of the sulfoxide activator determines whether one or two difluoroalkyl groups are incorporated into dearomatized products. Using TFAA can deliberately halt the reaction at the mono-difluoroalkylated dearomatized intermediate formed via a [3, 3]-rearrangement, which can be further trapped by external nucleophiles to give mono-difluoroalkylated alicycles. In contrast, switching to Tf2 O enhances the electrophilicity of dearomatized intermediates, thus allowing for the adoption of a second DFESE to produce dual-difluoroalkylated alicycles.