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Unveiling Potent Photooxidation Behavior of Catalytic Photoreductants

preprint
submitted on 13.01.2021, 00:36 and posted on 13.01.2021, 11:46 by Karina Targos, Oliver P. Williams, Zachary Wickens
We describe a photocatalytic system that reveals latent photooxidant behavior from one of the most reducing conventional photoredox catalysts, N-phenylphenothiazine (PTH). This aerobic photochemical reaction engages difficult to oxidize feedstocks, such as benzene, in C(sp2)–N coupling reactions through direct oxidation. Mechanistic studies are consistent with activation of PTH via photooxidation and that Lewis acid co-catalysts scavenge inhibitors formed upon catalyst activation.

Funding

Acknowledgment is made to the Donors of the American Chemical Society Petroleum Research Fund for partial funding of this research (60677-DNI1).

This material is based upon work supported by the National Science Foundation Graduate Research Fellowship Program under Grant No. DGE-1747503 (K.T.). Any opinions, findings, and conclusions or recommendations expressed in this material are those of the author(s) and do not necessarily reflect the views of the National Science Foundation.

Spectroscopic instrumentation was supported by a generous gift from Paul. J. and Margaret M. Bender, NSF (CHE-1048642), and NIH (S10OD012245 and 1S10OD020022-1).

History

Email Address of Submitting Author

wickens@wisc.edu

Institution

University of Wisconsin–Madison

Country

United States of America

ORCID For Submitting Author

0000-0002-5733-5288

Declaration of Conflict of Interest

no conflict of interest

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