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

Abstract

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.