4.8 Article

Unveiling Potent Photooxidation Behavior of Catalytic Photoreductants

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 143, Issue 11, Pages 4125-4132

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c00399

Keywords

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Funding

  1. Office of the Vice Chancellor for Research and Graduate Education at the University of Wisconsin-Madison
  2. Wisconsin Alumni Research Foundation
  3. American Chemical Society Petroleum Research Fund [60677-DNI1]
  4. National Science Foundation Graduate Research Fellowship Program [DGE-1747503]
  5. NSF [CHE-1048642]
  6. 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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