Benzo[b]furans were prepared in one pot based on the addition/palladium-catalyzed C-H bond functionalization of phenols with bromoalkynes. The addition reactions of phenols to bromoalkynes generated (Z)-2-bromovinyl phenyl ethers exclusively. Subsequent intramolecular cyclization affords 2-substituted benzo[b]furans in good yields through palladium-catalyzed direct C-H bond functionalizations.