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Pd(II)‐catalyzed 2‐aminoacetophenone oxime‐assisted sp2 and sp3 C─H arylation of aryl carboxamides is disclosed. The 2‐aminoacetophenone oxime is an N,N‐bidentate auxiliary that proceeds C─H activation through a six‐membered palladacycle intermediate, and the activation/functionalization on C(sp3)─H bond by the six‐membered ligand palladacycle is novel and achieved. This auxiliary facilitates the subsequent sp3 and sp2 C─H bond activation/functionalization in one step. The optimized protocol enables access to various aryl groups at the β‐sp2‐ and γ‐sp3‐centers of aryl carboxamides. The bidentate auxiliary is easy to synthesize on a gram scale, and we also described deoximination procedure after C─H functionalization. [ABSTRACT FROM AUTHOR]