Dearomatization of aryl sulfoxides: a switch between mono- and dual-difluoroalkylation |
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| Authors: | Xin Huang Yage Zhang Weijian Liang Qifeng Zhang Yaling Zhan Lichun Kong Bo Peng |
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| Institution: | Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Zhejiang Normal University, China, |
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| 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 Tf2O enhances the electrophilicity of dearomatized intermediates, thus allowing for the adoption of a second DFESE to produce dual-difluoroalkylated alicycles.Herein we describe the dearomatization of aryl sulfoxides with difluoroenol silyl ether (DFESE) using a rearrangement/addition protocol. |
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