Organocatalyzed Electrochemical Enantioselective α‐Alkylation of Aldehydes with 9,10‐Dihydroacridines

Abstract

Acridine scaffolds are present in biological and pharmaceutical molecules. However, achieving asymmetric functionalization of acridines remains challenging without an efficient and highly stereoselective approach. Here we demonstrate a facile electrooxidative asymmetric dehydrogenative coupling reaction of 9,10‐dihydroacridines with aldehydes. This method offers a sustainable and effective route to various chiral α‐alkylation of 9,10‐dihydroacridines in high yields with excellent enantioselectivities facilitated by readily available aminocatalyst. Detailed mechanistic studies and cyclic voltammetric analyses reveal that this asymmetric electrochemical reaction proceeds through redox‐mediated oxidation, followed by a nucleophilic attack with concurrently generated enamine. We anticipate that our research will open avenues for promising exploration in organocatalyzed electrochemical enantioselective transformations.