Herein, we disclose a new strategy that rapidly and reliably incorporates bromine atoms at distal, secondary C(sp3)–H sites in aliphatic amines with excellent and predictable site‐selectivity pattern. The resulting halogenated building blocks serve as versatile linchpins to enable a series of carbon‐carbon and carbon‐heteroatom bond‐formations at remote C(sp3) sites, thus offering a new modular and unified platform that expedites the access to advanced sp3 architectures possessing valuable nitrogen‐containing saturated heterocycles of interest in medicinal chemistry settings.