Visible-Light-Induced Pyridylation of Remote C(sp3)?H Bonds by Radical Translocation of N-Alkoxypyridinium Salts

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Title
Visible-Light-Induced Pyridylation of Remote C(sp3)?H Bonds by Radical Translocation of N-Alkoxypyridinium Salts
Author(s)
Inwon Kim; Bohyun Park; Gyumin Kang; Jiyun Kim; Hoimin Jung; Hyeonyeong Lee; Mu-Hyun Baik; Sungwoo Hong
Publication Date
2018-11
Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.57, no.47, pp.15517 - 15522
Publisher
WILEY-V C H VERLAG GMBH
Abstract
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. ⓒ 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinhei
URI
https://pr.ibs.re.kr/handle/8788114/5063
ISSN
1433-7851
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
Files in This Item:
H_Kim_et_al-2018-Angewandte_Chemie(Visible‐Light‐Induced Pyridylation).pdfDownload

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