An Iodide‐Mediated Anodic Amide Coupling

Abstract

The ubiquity of amide bonds, present in natural products and common pharmaceuticals renders this functional group one of the most prevalent in organic chemistry. Despite its importance and a wide variety of existing methods for its formation, the latter still can be a challenge for classical activating reagents such as chloridating agents or carbodii-mides. As the spent reagents often cannot be recycled, the development of more sustainable methods is highly desirable. Herein, we report an operationally simple and mild indirect electrochemical protocol to effect the condensation of carboxylic acids with amines, forming a wide variety of carboxamides.

PhNCO-enabled synthesis of secondary amides from N-(2-aminophenyl)benzamides

“…8,9 Over the last few decades, numerous stoichiometric coupling agents have emerged for carboxylic acid activation. 10–13 These methods have proven effective for various amides; however, the reagents tend to be toxic and hard to separate, unrecoverable waste is produced and these methods fall short in terms of adhering to the principles of green chemistry. Lately, various nonclassical strategies have been developed, such as amidation of aldehydes, 14,15 amino carbonylation of alkynes, 16 and oxidation of alcohols with amines.…”