Palladium-catalyzed arylation of β-methylene C(sp³)-H bonds at room temperature: Desymmetrization of simple cycloalkyl carboxylic acids

A new protocol for Pd-catalyzed β methylene C-H arylation of N-quinolyl cycloalkylcarboxamides with aryl iodides at room temperature is reported. The β methylene C-H bonds of symmetrical cycloalkylcarboxamides of varied ring size can be arylated in moderate to good yields and monoselectivity with excellent diastereoselectivity. This mono-selective β methylene C-H arylation reaction enabled the rapid synthesis of complex carbocycle products from easily accessible symmetrical cycloalkyl carboxylic acids via sequential C-H functionalization.