Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 143, Issue 11, Pages 4125-4132Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c00399
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Funding
- Office of the Vice Chancellor for Research and Graduate Education at the University of Wisconsin-Madison
- Wisconsin Alumni Research Foundation
- American Chemical Society Petroleum Research Fund [60677-DNI1]
- National Science Foundation Graduate Research Fellowship Program [DGE-1747503]
- NSF [CHE-1048642]
- NIH [S10OD012245, 1S10OD020022-1]
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The article introduces a photocatalytic system that utilizes N-phenylphenothiazine as a catalyst, revealing its latent photooxidant behavior. Experimental results show that PTH is activated through photooxidation, and Lewis acid cocatalysts are used to remove inhibitors formed during the reaction process.
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(sp(2))-N coupling reactions through direct oxidation. Mechanistic studies are consistent with activation of PTH via photooxidation and with Lewis acid cocatalysts scavenging inhibitors inextricably formed in this process.
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