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A cooperative indium(III)/silver(I) system for the synthesis of various five‐membered heterocycles, including dihydrofurans, pyrroles, spirolactones, and spiroiminolactones, through the sequential oxidative coupling/annulation reaction of 1,3‐dicarbonyl compounds with styrenes has been developed. Four different heterocyclic systems were successfully synthesized depending on the substitution pattern of the substrates using readily available starting materials. This system has the advantages of a broad substrate scope, moderate to good chemical yields, an operationally easy and simple procedure, and short reaction times.