This review immerses the multifaceted usefulness of o-halobenzyl halides as a pivotal substrates for the engineering of five- to nine-membered cyclic structures with the aid of transition metals as catalysts. These privileged entities engaged dual active sites, enabling the combination of both intermolecular benzylation and intramolecular arylation strategies that directs the formation of a diverse repository of cyclic structures. The entrance of transition-metal catalysis in cross-coupling transformations has sparked a revolution in forging aryl-heteroatom bonds, and culminating in the evolution of more potent synthetic methodologies for a wide spectrum of valuable compounds. Furthermore, the associated pharmaceutical and biological attributes of these cyclic structures augment their significance in medicinal chemistry research. This review aims to feature the importance of this synthetic methodology and its far-reaching applications in synthesis.