Nickel‐Catalyzed <i>N</i>‐Arylation of <i>NH</i>‐Sulfoximines with Aryl Halides via Paired Electrolysis
Dong Liu, Zhao‐Ran Liu, Cong Ma, Ke‐Jin Jiao, Bing Sun, Lei Wei, Julien Lefranc, Simon A. Herbert, Tian‐Sheng Mei
Abstract
Abstract A novel strategy for the N‐arylation of NH‐sulfoximines has been developed by merging nickel catalysis and electrochemistry (in an undivided cell), thereby providing a practical method for the construction of sulfoximine derivatives. Paired electrolysis is employed in this protocol, so a sacrificial anode is not required. Owing to the mild reaction conditions, excellent functional group tolerance and yield are achieved. A preliminary mechanistic study indicates that the anodic oxidation of a Ni II species is crucial to promote the reductive elimination of a C−N bond from the resulting Ni III species at room temperature.
Topics & Concepts
HalideElectrolysisNickelCatalysisArylAnodeElectrochemistryChemistryCombinatorial chemistryYield (engineering)Reductive eliminationInorganic chemistryOrganic chemistryMaterials scienceElectrodeMetallurgyElectrolytePhysical chemistryAlkylSynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques