We have established that trialkylborane-air, a readily available source of free radicals, enables hydrogen abstraction directly from sp3C-H bonds adjacent to the nitrogen atom of organic molecules, and successfully mediates subsequent coupling of the resultant alpha-aminoalkyl radicals with aldehydes or aryl isocyanates, providing unique access to nitrogen-containing molecular scaffolds. This presentation will disclose new insights into hydroxyalkylation and carbamoylation of alpha-nitrogen-substituted sp3C-H bonds of tertiary amines and lactams, as well as their application to the synthesis of bioactive compounds, with a view to highlighting a new design concept for organic synthesis.
