Rhodium (II)-catalyzed reactions of aryldiazoacetates can be conducted in the presence of iodide, triflate, organoboron, and organostannane functionality, resulting in the formation of a variety of cyclopropanes or CH insertion products with high stereoselectivity. The combination of the rhodium (II)-catalyzed reaction with a subsequent palladium (II)-catalyzed Suzuki coupling offers a novel strategy for diversity synthesis.