Herein, we report a practical and efficient methodology for synthesizing highly valuable sulfoximine- and silicon-substituted carboxylamides from copper-catalyzed remote C(sp3)-H sulfoximination and silylation of N-fluorocarboxamides under ambient conditions. The copper-catalyzed reactions proceed to undergo sequential single-electron transfer (SET), 1,5-hydrogen atom transfer (1,5-HAT), and cross-coupling steps, thus generating new C-N and C-Si bonds. Significantly, this practical transformation occurs under mild conditions and exhibits a broad substrate scope and high regioselectivity.