α,β-unsaturated silyl esters are an important class of compounds in organic, inorganic and pharmaceutical chemistry, known for their versatility and unique reactivity. The conjugated system in these compounds enables for Michael addition reactions, making them useful intermediates in the synthesis of complex organic/inorganic molecules, including pharmaceuticals, agrochemicals, and natural products. Having realized the importance of α,β-unsaturated silyl esters, we have devised a strategy to synthesize various functionalized allyl and vinyl silanes using diazo compounds and respective silanes. Herein we have demonstrated that the allyl and vinyl silanes can react with diazo compounds in a chemoselective manner offering a versatile method for constructing C-C bond formation over the cyclopropanation reaction in the presence of 1 mol% of [Cp*RuCl2]n as a catalyst under mild conditions. Direct C-H bond functionalization of allyl and vinyl silanes with alpha diazo esters and phosphonate diazo showcasing the adaptability of silicon-based chemistry in modern organic synthesis. The plausible mechanism of the reaction has been realized with the help of DFT calculations. All the synthesized α,β-unsaturated siliyl esters were isolated and characterized by using sophisticated analytical and spectroscopic techniques.