The Merger of Aryl Radical-Mediated Halogen-Atom Transfer (XAT) and Copper Catalysis for the Modular Cross-Coupling-Type Functionalization of Alkyl Iodides

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.

Automated summary

Here, a toolbox strategy for cross-coupling unactivated secondary alkyl iodides with various N-, O-, and C-based nucleophiles is described. This strategy utilizes photoredox-generated phenyl radicals to mediate halogen-atom transfer (XAT) and convert alkyl iodides into corresponding radicals. These radicals then undergo a second catalytic cycle mediated by copper, enabling C-N/O/C bond formation with the nucleophiles.