Palladium (II) Catalyzed Synthesis of Meta-Substituted Biphenyls via Carboxylate Directed Ortho-Arylation Decarboxylation Cascade: Experimental and Theoretical Insights

Abstract

The ortho-directing nature of the carboxylic acid functional group has been utilized in the traceless C6 arylation of C2-substituted benzoic acids with aryl iodides under palladium catalysis to afford meta-substituted biphenyls. The reaction is seen to follow a cascade pathway involving traceless carboxylate directed C2 arylation followed by decarboxylation. The utilization of a bulky protic solvent such as pivalic acid removes the need of higher amounts of the arylating agents as required in the earlier protocols. Theoretical studies further reveal the tandem directed arylation–decarboxylation pathway.