Abstract
This report describes the development of a visible-light photocatalytic system for C(sp2)-H amination that leverages in situ-generated photocatalysts. We demonstrate that the combination of acridine derivatives and Lewis acids form potent photooxidants that promote the C-H amination of electronically diverse arenes upon irradiation with visible-light (440 nm). A first-generation photocatalyst composed of Sc (OTf)3 and acridine effects the C-H amination of substrates with oxidation potentials ≤ +2.5 V vs SCE with pyrazole, triazole, and pyridine nucleophiles. Furthermore, the simplicity and modularity of this system enable variation of both Lewis acid and acridine to tune reactivity. This enabled the rapid identification of two second-generation photocatalysts (derived from (i) Al(OTf)3 and acridine or (ii) Sc(OTf)3 and a pyridinium-substituted acridine) that catalyze a particularly challenging transformation: C(sp2)-H amination with benzene as the limiting reagent.
Recommended Citation
M. R. Lasky et al., "Visible-Light Photocatalytic C-H Amination Of Arenes Utilizing Acridine-Lewis Acid Complexes," Journal of the American Chemical Society, vol. 146, no. 21, pp. 14799 - 14806, American Chemical Society, May 2024.
The definitive version is available at https://doi.org/10.1021/jacs.4c02991
Department(s)
Chemistry
International Standard Serial Number (ISSN)
1520-5126; 0002-7863
Document Type
Article - Journal
Document Version
Citation
File Type
text
Language(s)
English
Rights
© 2025 American Chemical Society, All rights reserved.
Publication Date
29 May 2024
PubMed ID
38759094
Comments
Dow Chemical Company, Grant R35GM1361332