The development of a general and selective method for alpha-C-(sp(3))-H silylation of feedstock amines has been a long-standing challenge. In this paper, we disclose a mild, general, practical, and highly regio- and diastereoselective alpha-C-(sp(3))-H silylation of various readily available acyclic, cyclic, and aromatic amines with silylboranes through a copper-catalyzed intramolecular 1,5-hydrogen atom transfer (HAT) strategy. The mild activation of 2-iodobenzamide to generate an aryl radical enabled by a ligand-coordinated silyl copper complex without additional heating or photoinduced cond...