PhB(OH)<sub>2</sub>-Promoted Electrochemical Sulfuration–Formyloxylation of Styrenes and Selectfluor-Mediated Oxidation–Olefination
Yulei Zhao, Xuqiang Guo, Shuai Li, Yuhang Fan, Xuejun Sun, Laijin Tian
Abstract
We report a PhB(OH)2-promoted electrochemical sulfuration–formyloxylation reaction of styrenes employing commercially available thiophenols/thiols as thiolating agents. Specifically, metal catalysts and external chemical oxidants are not needed in the reaction for the formation of β-formyloxy sulfides, and these sulfides can be further converted to (E)-vinyl sulfones via the Selectfluor-mediated oxidation–olefination. Notably, on the basis of this electrochemical oxidation strategy, β-hydroxy sulfide, β-formyloxy sulfoxide, β-formyloxy sulfone, and (E)-vinyl sulfoxide can also be easily prepared.
Topics & Concepts
SelectfluorChemistrySulfoxideElectrochemistrySulfideSulfoneCatalysisDimethyl sulfoxideOrganic chemistryStyreneCombinatorial chemistryCopolymerElectrodePolymerPhysical chemistrySulfur-Based Synthesis TechniquesRadical Photochemical ReactionsChemical Synthesis and Reactions