The presence of nitrogen-based functionality in natural products has allowed for optimal interactions with biomolecular targets, a characteristic that makes them blueprints for drug discovery. However, despite continual progress, the development of methodology for direct C–N bond formation still remains a significant challenge. In an effort to improve C-–N bond formation, this project aims to develop a new strategy to incorporate amine functionality into a range of organic molecules by merging radical reactions with nitroso chemistry. The primary focus is to synthesize benzylic amines through the copper catalyzed addition of benzylic radicals across various arylnitroso compounds to form hydroxylamine dimers. The resulting dimer intermediates can subsequently be reduced with zinc under acidic conditions to form the desired benzylic amines.