<i>N</i>‑Hydroxyphthalimides as Nitrogen\nRadical Precursors in the Copper-Catalyzed Radical Cross-Coupling\nAmination of Arylboronic Acids: Synthesis of Arylamines

A new and practical approach for the synthesis of arylamines\nvia\ncopper-catalyzed radical cross-coupling amination of arylboronic acids\nhas been developed. The key enabling advance in this protocol is the\ndesign of <i>N</i>-hydroxyphthalimides as precursors to\ngenerate nitrogen-based radical intermediates for cross-coupling with\narylboronic acids, providing the corresponding arylamines of a high\nyield of up to 98%. In addition, the procedure successfully demonstrated\nremarkable efficiency across a wide range of functional group tolerances.\nMechanistic investigations suggested that a nitrogen radical cross-coupling\npathway is possible via phosphite-mediated N–O bond scission.