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

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Title
Visible-light-induced cascade radical ring-closure and pyridylation for the synthesis of tetrahydrofurans
Author(s)
Yechan Kim; Kangjae Lee; Gangadhar Rao Mathi; Inwon Kim; Sungwoo Hong
Publication Date
2019-04
Journal
GREEN CHEMISTRY, v.21, no.8, pp.2082 - 2087
Publisher
ROYAL SOC CHEMISTRY
Abstract
© 2019 The Royal Society of Chemistry. 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
URI
https://pr.ibs.re.kr/handle/8788114/6470
ISSN
1463-9262
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Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
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