9-Mesitylacridinium salts are widely recognized as efficient organic photoredox catalysts owing to their strong excited-state oxidizing power and stability under visible-light irradiation. In this study, a new mesityl acridinium derivative bearing a di-tert-butylphenyl substituent on the nitrogen atom was synthesized. The introduction of tert-butyl groups on the N-aryl moiety was primarily aimed at improving solubility and chemical stability of the acridinium salt. Starting from a 9(10H)-acridinone precursor, the target compound was obtained in high overall yield through a concise synthetic sequence. The synthesis consists of a copper-catalyzed C–N coupling reaction to install the aryl substituent on the nitrogen atom, followed by a Grignard reaction and subsequent acid treatment to afford the corresponding acridinium salt. All transformations proceeded smoothly, providing efficient access to the desired novel acridinium derivative. This work presents a practical example of the structural modification of mesitylacridinium derivatives directed toward enhanced solubility and stability, and provides a useful synthetic platform for the preparation of structurally diverse acridinium salts.
Itabashi et al. (Tue,) studied this question.