The Merger of Aryl Radical-Mediated Halogen-Atom Transfer (XAT) and Copper Catalysis for the Modular Cross-Coupling-Type Functionalization of Alkyl Iodides
Lewis Caiger, Huaibo Zhao, Timothée Constantin, James J. Douglas, Daniele Leonori
Abstract
Here, we report a toolbox strategy to cross-couple unactivated secondary alkyl iodides with various N-, O-, and C-based nucleophiles. This strategy harnesses the ability of photoredox-generated phenyl radicals to mediate halogen-atom transfer (XAT) and convert alkyl iodides into the corresponding radicals. These species engage in a second catalytic cycle, mediated by copper, which enables C–N/O/C bond formation with the various nucleophiles.
Topics & Concepts
ChemistryNucleophileAlkylArylHalogenCatalysisRadicalPhotoredox catalysisPhotochemistryCatalytic cycleCombinatorial chemistryOrganic chemistryPhotocatalysisRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques