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Photoinduced α-C−H Amination of Cyclic Amine Scaffolds Enabled by Polar-Radical Relay

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Title
Photoinduced α-C−H Amination of Cyclic Amine Scaffolds Enabled by Polar-Radical Relay
Author(s)
Wongyu Lee; Dongwook Kim; Sangwon Seo; Sukbok Chang
Publication Date
2022-06
Journal
Angewandte Chemie - International Edition, v.61, no.25
Publisher
John Wiley and Sons Inc
Abstract
© 2022 Wiley-VCH GmbH.Herein, we report a polar-radical relay strategy for α-C−H amination of cyclic amines with N-chloro-N-sodio-carbamates. The relay is initiated by in situ generation of cyclic iminium intermediate using N-iodosuccinimide (NIS) oxidant as an initiator, which then operates through a series of polar (addition and elimination) and radical (homolysis, hydrogen- and halogen atom transfer) reactions to enable the challenging C−N bond formation in a controlled manner. A broad range of α-amino cyclic amines were readily accessed with excellent regioselectivity, and the superb applicability was further demonstrated by functionalization of biologically relevant compounds.
URI
https://pr.ibs.re.kr/handle/8788114/11923
DOI
10.1002/anie.202202971
ISSN
1433-7851
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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