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

18 May 2020, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Red light has the advantages of low energy, less health risk and high penetration depth through various media. Herein, a helical carbenium ion (N,N’-di-n-propyl-1,13-dimethoxyquinacridinium (nPr-DMQA+) tetrafluoroborate) has been used as an organic photoredox catalyst for photoreductions and photooxidations in the presence of red light (λmax = 640 nm). It has catalyzed red-light-mediated dual transition-metal/photoredox-catalyzed C-H arylation and intermolecular atom transfer radical addition through oxidative quenching, affording products in 57-93% yields. 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, delivering products in up to 92% yield. Thus, a versatile organic photoredox catalyst (helical carbenium ion) for red-light-mediated photoredox reactions has been developed.


Organic photocatalyst
red-light-mediated photocatalysis


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