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A palladium-catalyzed cross-coupling reaction of 2-alkylphenyl bromides with biphenylene has been developed. The reactions formed eight-membered carbocycles through C(sp 3 )-H activation and the formation of two C-C bonds, and the chiral products were obtained with excellent diastereoselectivity. The reaction provides a new strategy for the construction of eight-membered carbocycles, and the products represent a novel type of chiral scaffold.