Comprehensive Summary We developed a novel Pd‐catalyzed carbonylation of ortho ‐alkenyl iodobenzenes with CO, affording a diverse array of 3‐arylindenones in good to excellent yields (up to 94% yield). This methodology exhibits broad substrate scope and good functional group compatibility. The synthetic utility was demonstrated by a gram‐scale reaction, diverse product derivatizations, and the preparation of an intermediate for a PPARγ agonist.