A tandem, one-pot reaction of 2,3-dibromoindenone with phenols is reported, which provides a straightforward approach to accomplish structurally diverse indenobenzofurans in excellent yields. Besides, the control experiments revealed that reaction proceeds through a two-step sequence via an intermolecular Michael addition-elimination reaction, which enables the C−O bond formation, followed by palladium-catalyzed intramolecular C−C bond formation through C−H activation. Significantly, this protocol offers a convenient approach to synthesize the diverse tetracyclic indenobenzofurans. © 2022 Arkat. All rights reserved.