Regioselective Nucleophilic Diamination of Quinones Enabling Access to 3,5-, 3,6-, and Mixed Diamino Derivatives: Synthesis and Photocurrent Characterization

Abstract

In this study, we disclose a Cu(OTf)2-catalyzed regioselective nucleophilic amination of quinones to synthesize 3,5-, 3,6-, and mixed diaminoquinones under air. The regioselectivity, controlled by the catalyst coordination and the steric hindrance of amines, follows different patterns: the reactions with anilines afforded the 3,6-diaminoquinones; the coupling with aliphatic primary amines led to the formation of a mixture of 3,6- and 3,5-isomers; and the use of sterically hindered secondary amines delivered the 3,5-isomers. Furthermore, we found that the synthesized diaminoquinones exhibited stable and strong photocurrent responses, suggesting potential applications in optoelectronic materials.