Visible-Light SNAr Pyridination of Aryl Halides and Triflates with Acridine-Lewis Acid Photocatalysts
- 15 July 2025
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 90 (29) , 10332-10337
Abstract
This report describes the development of a visible light (440 nm) photocatalytic method for the cation radical-accelerated (CRA) SNAr pyridination of aryl (pseudo)halides using modular acridine-Lewis acid photocatalysts. A first-generation catalyst composed of acridine and Sc(OTf)3 is effective for the reaction of electronically diverse pyridines with electron-rich (primarily alkoxy- and alkyl-substituted) aryl chlorides and triflates. With select substrate pairs, an alternative electron donor-acceptor pathway can also be operative. Modifying the acridine backbone of the in situ photocatalyst broadens the scope of aryl chloride coupling partners, enabling visible light CRA-SNAr with unactivated chlorobenzene derivatives as the limiting reagent.Keywords
Funding Information
- Horace H. Rackham School of Graduate Studies, University of Michigan
- National Institute of General Medical Sciences (R35GM1361332)
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