Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 28, Pages 12056-12061Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c05507
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- University of Arizona
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Red light has the advantages of low energy, less health risks, 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 (lambda(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(sp(3))-H oxygenation through reductive quenching. Thus, a versatile organic photoredox catalyst (helical carbenium ion) for red-light-mediated photoredox reactions has been developed.
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