The construction of C(sp)-C(sp) bonds is pivotal in organic synthesis; however, traditional methods involving alkyl halides are often limited by substrate tolerance and bond dissociation energies, particularly with alkyl fluorides. Herein, we report a silylboronate-mediated cross-coupling strategy that circumvents these challenges, enabling the efficient formation of C(sp)-C(sp) bonds between alkyl fluorides and aryl alkanes under mild conditions. Various alkyl fluorides have also been effectively utilized, demonstrating the versatility and broad applicability of this approach. The use of diglyme is critical for this transformation which encapsulates potassium cations and enhances the reaction efficiency. Conventional alkyl halides, including chlorides, bromides, and iodides, are also suitable for this transformation. Density functional theory (DFT) calculations were conducted on the silylboronate-mediated coupling reactions for the first time. Interestingly, while experimental results suggest a radical mechanism, DFT calculations indicate a preference for an ionic pathway.