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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.

A palladium-catalyzed cross-coupling reaction of aryl halides with 2-chlorobenzoic acids has been developed. The reaction forms C(sp3), C(sp2)-palladacycles through C(sp3)-H activation. The palladacycles react with 2-chlorobenzoic acids through two successive C-C cross-couplings, and two C-C bonds are formed with high chemoselectivity. The reaction provides an innovative method for the synthesis of 9,10-dihydrophenanthrenes.