The first palladium-catalyzed C-O bond formation method for the synthesis of silacarboxylates by silacarboxylic acids with a broad range of aryl iodides and iodo-N-heterocycles is reported. Electron-deficient, electron-rich, and sterically hindered aryl iodides were well-tolerated to furnish the corresponding aryl silacarboxylates in moderate to excellent yields. Active functional groups, such as -NH2, -CHO, and allyl-, showed good tolerance, even in the large-scale synthesis. Double and triple esterification were also demonstrated to be effective.