Helical Carbenium Ion: A Versatile Organic Photoredox Catalyst for Red-Light-Mediated Reactions

Abstract

Red light has the advantages of low energy, less health risks, and high penetration depth through various media. Herein, a helical carbenium ion (<i>N,N'</i>-di-<i>n</i>-propyl-1,13-dimethoxyquinacridinium (^<i>n</i>Pr-DMQA⁺) tetrafluoroborate) has been used as an organic photoredox catalyst for photoreductions and photooxidations in the presence of red light (λ_max = 640 nm). It has catalyzed red-light-mediated dual transition-metal/photo-redox-catalyzed C-H arylation and intermolecular atom-transfer radical addition through oxidative quenching. Moreover, its potential in photooxidation catalysis has also been demonstrated by successful applications in red-light-induced aerobic oxidative hydroxylation of arylboronic acids and benzylic C(sp³)-H oxygenation through reductive quenching. Thus, a versatile organic photoredox catalyst (helical carbenium ion) for red-light-mediated photoredox reactions has been developed.