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A palladium‐catalyzed chemoselective coupling of readily available bicyclo[1.1.1]pentanyl alcohols (BCP−OH) with various halides is reported, which offers expedient approaches to a wide range of cyclobutanone and β,γ‐enone skeletons via single or double C−C activation. The chemistry shows a broad substrate scope in terms of both the range of BCP−OH and halides including a series of natural product derivatives. Moreover, dependency of reaction chemodivergence on base additive has been investigated through experimental and density functional theory (DFT) studies, which is expected to significantly enrich the reaction modes and increase the synthetic potential of BCP−OH in preparing more complex molecules. [ABSTRACT FROM AUTHOR]