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The rhodium(III)‐catalyzed aromatic CH activation/intramolecular Heck‐type reaction has been studied to synthesize spirocyclic compounds, an important class of molecules in medicinal chemistry and natural product synthesis. This approach was efficient with a variety of substituted N‐methoxybenzamides tethered to different cyclic alkenes having a 5‐, 6‐ or 7‐membered ring. This practical method affords sterically hindered o‐substituted aryl spirocycles that are valuable compounds for further functionalization to access relevant building blocks.