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

Liangyong Mei, Jose M Veleta, thomas Gianetti
2020 unpublished
<div><p><a></a><a></a><a></a><a>Red light has the advantages of low energy, less health risk and high penetration depth through various media. Herein, </a>a <a>helical carbenium ion (</a><i>N,N'</i>-di-<i>n</i>-propyl-1,13-dimethoxyquinacridinium (<i><sup>n</sup></i>Pr-DMQA<sup>+</sup>) tetrafluoroborate) has been used as an organic photoredox catalyst for photoreductions and photooxidations in the presence of red light (λ<sub>max</sub> = 640 nm). It has catalyzed red-light-mediated dual
more » ... ediated 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(sp<sup>3</sup>)-H oxygenation through reductive quenching, delivering products in up to 92% yield. Thus, a versatile organic photoredox catalyst (helical carbenium ion)<b> </b>for red-light-mediated photoredox reactions has been developed.</p></div>
doi:10.26434/chemrxiv.12316154.v1 fatcat:lm557vkpnzalzhgwyw5h3pmj6i