Redox-Neutral Cross-Coupling Amination with Weak <i>N-</i>Nucleophiles: Arylation of Anilines, Sulfonamides, Sulfoximines, Carbamates, and Imines via Nickelaelectrocatalysis
Chen Zhu, Ajit Prabhakar Kale, Huifeng Yue, Magnus Rueping
Abstract
nucleophiles, including anilines, sulfonamides, sulfoximines, carbamates, and imines via concerted paired electrolysis. Notably, electron-deficient anilines and sulfonamides are also suitable substrates. Interestingly, when benzophenone imine is applied in the arylation, the product selectivity toward the formation of amine and imine product can be addressed by a base switch. In addition, the alternating current mode can be successfully applied. DFT calculations support a facilitated reductive elimination pathway.
Topics & Concepts
NucleophileChemistryAminationImineBenzophenoneArylAmine gas treatingCombinatorial chemistrySelectivityElectrolysisHalideOrganic chemistryPhotochemistryCatalysisElectrolytePhysical chemistryAlkylElectrodeCatalytic C–H Functionalization MethodsSulfur-Based Synthesis TechniquesCatalytic Cross-Coupling Reactions