Catalytic I2-moist DMSO-mediated synthesis of valuable α-amidohydroxyketones and unsymmetrical gem-bisamides from benzimidates

We developed an efficient and straightforward I-2-catalyzed strategy for the synthesis of functionalized alpha-amidohydroxyketones and symmetrical and unsymmetrical bisamides using incipient benzimidate scaffolds as starting materials and moist-DMSO as a reagent and solvent. The developed method proceeds through chemoselective intermolecular N-C-bond formation of benzimidates and the alpha-C(sp(3))-H bond of acetophenone moieties. The key advantages of these design approaches include broad substrate scope and moderate yields. High-resolution mass spectrometry of the reaction progress and labeling experiments provided suitable evidence regarding the possible mechanism. H-1 nuclear magnetic resonance titration revealed notable interaction between the synthesized alpha-amidohydroxyketones and some anions as well as biologically important molecules, which revealed a promising recognition property of these valuable motifs.

Automated summary

We developed an efficient I-2-catalyzed strategy for the synthesis of functionalized alpha-amidohydroxyketones and symmetrical and unsymmetrical bisamides using benzimidate scaffolds and moist-DMSO. The broad substrate scope and moderate yields are the key advantages of this approach. High-resolution mass spectrometry and labeling experiments provided evidence for the mechanism, and H-1 nuclear magnetic resonance titration revealed the recognition property of the synthesized compounds.