Visible-light-induced cascade radical ring-closure and pyridylation for the synthesis of tetrahydrofurans

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Reported is a novel visible-light-enabled alkoxy radical ring-closure and pyridylation from N-alkenyloxypyridinium salts serving as both alkoxy radical precursors and heteroaryl sources. This strategy features a photoredox tandem radical process involving a sequential fragmentation of an N-alkoxypyridinium salt, a radical cyclization process, and a pyridylation process. This method exhibited broad substrate scope, good functional group compatibility, and metal-free mild conditions, offering a powerful synthetic tool for assembling various pyridine-tethered tetrahydrofurans and late-stage functionalization of complex biorelevant molecules. Moreover, radical cascade cyclization could be successfully achieved, leading to the synthesis of previously challenging and important pyridine-tethered bicyclic oxaspiro ring systems.
Publisher
ROYAL SOC CHEMISTRY
Issue Date
2019-04
Language
English
Article Type
Article
Citation

GREEN CHEMISTRY, v.21, no.8, pp.2082 - 2087

ISSN
1463-9262
DOI
10.1039/c9gc00414a
URI
http://hdl.handle.net/10203/261835
Appears in Collection
CH-Journal Papers(저널논문)
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