not-yet-known not-yet-known not-yet-known unknown Text：The strategic incorporation of the pharmacologically privileged trifluoroethyl group into the biologically significant benzofuran scaffold offers considerable potential for medicinal and agrochemical applications. Herein, we report an atom-economical synthetic approach to 3-trifluoroethyl benzofurans through Rh-catalyzed cascade reaction of readily available trifluoromethyl alkene-tethered benzocyclobutenols. This transformation proceeds via a mechanistically intricate sequence involving C−C bond activation, migratory insertion, β-hydride elimination, chain walking, and transfer hydrogenation. A key challenge in this process, namely the selective β-H elimination of α-trifluoromethyl alkylrhodium species with the suppression of the β-F elimination, has been addressed through transfer hydrogenation strategy. By modulation of reaction conditions, both intermolecular and intramolecular transfer hydrogenation pathways have been developed, leading to the divergent synthesis of 4-β-keto and 4-β-hydroxy substituted 3-trifluoroethyl benzofurans. To our knowledge, this work represents the first general and practical synthetic method for 3-trifluoroethyl benzofurans.