One-pot synthesis of amides from aryloyl peroxides and aldimines in dimethyl sulfoxide

Abstract

A novel method for amide synthesis from aldimines using an aryloyl peroxide/DMSO system has been developed. The acyl groups of the resulting amides are derived from the aryloyl peroxide, while the N-containing motifs originate from the aldimines. Mechanistic investigations reveal that the aryloyl peroxide reacts with DMSO to form an anhydride, which is partially hydrolyzed to produce a carboxylic acid. This acid catalyzes the hydrolysis of aldimines to controllably release amines, which then react with the anhydride to selectively form amides. This approach offers controlled reaction and product selectivity, avoiding byproduct formation from direct arylamine oxidation by BPO. This mild one-pot method not only provides a route for the synthesis of amides from aldimines, but also demonstrates the feasibility of synthesizing amides from amines, thereby expanding the scope of organic synthesis strategies.