Boron-Catalyzed Michael Reaction of Donor–Acceptor Carboxylic Acid Pairs Enabling Direct Synthesis of 1,5-Dicarboxylic Acids

A boron-catalyzed Michael reaction using pairs of carboxylic acids was developed. The reaction occurs through dual activation of the two substrates by a boron catalyst, which facilitates boron enolate formation from the donor carboxylic acid with simultaneous activation of the α,β-unsaturated carboxylic acid as the acceptor. α-Aryl and α-alkenyl carboxylic acids were applicable as donors. The versatility and utility of this reaction were demonstrated by the direct use of pharmaceuticals as donor carboxylic acids.