Rh(III)-catalyzed redox-neutral chemodivergent coupling of -phenoxyacetamides and alkylidenecyclopropanes (ACPs) has been documented. The reaction proceeds C-H activation, regioselective migratory insertion and stereoselective β-carbon elimination followed by β-hydride elimination, resulting in -dienylation of phenols in nonpolar solvents, whereas [3 + 2]-annulation leading to dihydrobenzofurans was realized in polar fluorinated solvents. It was observed that the nucleophilic directing group controls the elimination of β-carbon and so plays a vital role for achieving high stereoselectivities. The synthetic utility of the dienylation and annulation was demonstrated by carrying out gram scale reactions and further derivatization.