Development of boronic acid catalysts for direct amidation of aromatic carboxylic acids using fluorescence-based screening

Abstract

Direct amidation of carboxylic acids with amines holds significant importance; therefore, catalytic processes involving boronic acids have undergone extensive investigation. However, studies focused on the amidation of aromatic carboxylic acids remain limited. In this study, we introduce a fluorescence-based screening methodology employing an anthracene derivative probe, facilitating the rapid evaluation of various amidation catalysts. Using this approach, boronic acids were evaluated for their catalytic potential. Our findings reveal that 2-hydroxyphenylboronic acid (C7), previously deemed inefficient for aliphatic acids, effectively catalyzes the amidation of aromatic acids. The catalysts identified through this method consistently achieved high yields, reaching up to 98% across a broad spectrum of substrates. © 2024 The Royal Society of Chemistry.