Rhodium-catalyzed chelation-assisted C-H bond functionalization reactions have been extensively studied, offering a promising alternative to traditional cross-coupling methods. This approach enables the direct functionalization of unfunctionalized precursors, bypassing the need for pre-functionalization, which is costly and reduces reagent availability. The use of chelating directing groups enhances substrate scope and applicability in total synthesis. Rhodium-based catalysts, particularly Rh(I) and Rh(III), have been pivotal in developing efficient methods for C-H bond activation, including alkylation, oxidative coupling, and functionalization of polar π bonds such as those in imines and isocyanates. These methods have been applied to the synthesis of complex molecules, including natural products and pharmaceuticals, demonstrating their utility in organic synthesis. The development of enantioselective strategies has further expanded the scope of these reactions, enabling the synthesis of chiral compounds with high stereoselectivity. The mechanisms of these reactions involve chelation-assisted activation of C-H bonds, followed by reductive elimination and other steps to form new bonds. The use of chiral ligands and auxiliary groups has been crucial in achieving enantioselectivity. The study highlights the versatility of rhodium-catalyzed C-H bond functionalization in various transformations, including annulations, alkenylation, and electrocyclization, with applications in the synthesis of complex structures such as pyridines, dihydropyridines, and bicyclic enamines. The ongoing research aims to broaden the scope of these reactions, incorporating a wider range of directing groups and electrophiles, to further enhance their utility in synthetic chemistry.Rhodium-catalyzed chelation-assisted C-H bond functionalization reactions have been extensively studied, offering a promising alternative to traditional cross-coupling methods. This approach enables the direct functionalization of unfunctionalized precursors, bypassing the need for pre-functionalization, which is costly and reduces reagent availability. The use of chelating directing groups enhances substrate scope and applicability in total synthesis. Rhodium-based catalysts, particularly Rh(I) and Rh(III), have been pivotal in developing efficient methods for C-H bond activation, including alkylation, oxidative coupling, and functionalization of polar π bonds such as those in imines and isocyanates. These methods have been applied to the synthesis of complex molecules, including natural products and pharmaceuticals, demonstrating their utility in organic synthesis. The development of enantioselective strategies has further expanded the scope of these reactions, enabling the synthesis of chiral compounds with high stereoselectivity. The mechanisms of these reactions involve chelation-assisted activation of C-H bonds, followed by reductive elimination and other steps to form new bonds. The use of chiral ligands and auxiliary groups has been crucial in achieving enantioselectivity. The study highlights the versatility of rhodium-catalyzed C-H bond functionalization in various transformations, including annulations, alkenylation, and electrocyclization, with applications in the synthesis of complex structures such as pyridines, dihydropyridines, and bicyclic enamines. The ongoing research aims to broaden the scope of these reactions, incorporating a wider range of directing groups and electrophiles, to further enhance their utility in synthetic chemistry.