Visible-Light-Induced Pyridylation of Remote C(sp<sup>3</sup>)−H Bonds by Radical Translocation of N-Alkoxypyridinium Salts

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Metal-free, visible-light-induced site-selective heteroarylation of remote C(sp3)−H bonds has been accomplished through the design of N-alkoxyheteroarenium salts serving as both alkoxy radical precursors and heteroaryl sources. The transient alkoxy radical can be generated by the single-electron reduction of an N-alkoxypyridinium substrate by a photoexcited quinolinone catalyst. Subsequent radical translocation of the alkoxy radical forms a nucleophilic alkyl radical intermediate, which undergoes addition to the substrate to achieve remote C(sp3)−H heteroarylation. This cascade strategy provides a powerful platform for remote C(sp3)−H heteroarylation in a controllable and selective manner and is well suited for late-stage functionalization of complex bioactive molecules.
Publisher
WILEY-V C H VERLAG GMBH
Issue Date
2018-11
Language
English
Article Type
Article
Citation

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.57, no.47, pp.15517 - 15522

ISSN
1433-7851
DOI
10.1002/anie.201809879
URI
http://hdl.handle.net/10203/247629
Appears in Collection
CH-Journal Papers(저널논문)
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