Nickela‐electrocatalyzed Mild C−H Alkylations at Room Temperature
Ramesh C. Samanta, Julia Struwe, Lutz Ackermann
Abstract
Direct alkylations of carboxylic acid derivatives are challenging and particularly nickel catalysis commonly requires high reaction temperatures and strong bases, translating into limited substrate scope. Herein, nickel-catalyzed C-H alkylations of unactivated 8-aminoquinoline amides have been realized under exceedingly mild conditions, namely at room temperature, with a mild base and a user-friendly electrochemical setup. This electrocatalyzed C-H alkylation displays high functional group tolerance and is applicable to both the primary and secondary alkylation. Based on detailed mechanistic studies, a nickel(II/III/I) catalytic manifold has been proposed.
Topics & Concepts
AlkylationCatalysisNickelPrimary (astronomy)ChemistrySubstrate (aquarium)Scope (computer science)Combinatorial chemistryFunctional groupBrønsted–Lowry acid–base theoryBase (topology)Manifold (fluid mechanics)ElectrochemistryOrganic chemistryComputer sciencePhysical chemistryPhysicsAstronomyPolymerProgramming languageMathematical analysisMathematicsGeologyElectrodeOceanographyMechanical engineeringEngineeringCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsAsymmetric Hydrogenation and Catalysis