The nickel(II)-catalyzed direct benzylation, allylation, alkylation, and methylation of C-H bonds in aromatic amides containing an 8-aminoquinoline moiety as the directing group

Abstract

Direct alkylation via the cleavage of the ortho C-H bonds by a nickel-catalyzed reaction of aromatic amides containing an 8-aminoquinoline moiety as the directing group with alkyl halides is reported. Various alkyl halides, including benzyl, allyl, alkyl, and methyl halides (or pseudo halides) participate as electrophilic coupling partners. The reaction shows a high functional group compatibility. The reaction proceeds in a highly regioselective manner at the less hindered C-H bonds in the reaction of meta-substituted aromatic amides, irrespective of the electronic nature of the substituent. The mechanism responsible for the C-H alkylation reaction is discussed based on the results obtained in a variety of mechanistic experiments.