Dual Photoredox/Nickel-Promoted Alkylation of Heteroaryl Halides with Redox-Active Esters
Nicole Erin Behnke, Zachary S. Sales, Minyan Li, Aaron T. Herrmann
Abstract
Herein a method for the radical alkylation of heteroaryl halides that relies upon the combination of photoredox and nickel catalysis is described. The use of aliphatic N-(acyloxy)phthalimides as redox-active esters affords primary and secondary radicals for the decarboxylative dual cross-coupling with pyrimidine and pyridine heteroaryl chlorides, bromides, and iodides. The method provides an additional synthetic tool for the incorporation of medicinally relevant heterocyclic motifs.
Topics & Concepts
ChemistryAlkylationHalidePyridinePhotoredox catalysisNickelPhthalimidesRadicalRedoxCatalysisCombinatorial chemistryPyrimidinePrimary (astronomy)Organic chemistryStereochemistryPhthalimidePhotocatalysisAstronomyPhysicsRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques