Nickel‐Catalyzed Electrosynthesis of Aryl and Vinyl Phosphinates
Farah Daili, Abdelhakim Ouarti, Marine Pinaud, Ibtihal Kribii, Stéphane Sengmany, Erwan Le Gall, Éric Léonel
Abstract
A mild and useful nickel‐catalyzed electrochemical phosphonylation of aryl and vinyl bromides is described. We show that alkyl H ‐phenylphosphinates can be coupled electrochemically with functionalized aryl and vinyl bromides using very simple conditions (Fe/Ni anode, bench‐stable nickel pre‐catalyst, undivided cell, galvanostatic electrolysis) to furnish the corresponding aryl and vinyl phosphinates in satisfactory to good yields. Couplings can also be applied to heteroaromatic bromides with some limitations like increased propensity to hydro‐dehalogenation.
Topics & Concepts
ElectrosynthesisArylChemistryNickelElectrolysisCatalysisElectrochemistryHalogenationAlkylAnodeOrganic chemistryElectrodePhysical chemistryElectrolyteRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods