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Functionalization of Pyridinium Derivatives with 1,4-Dihydropyridines Enabled by Photoinduced Charge Transfer

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Title
Functionalization of Pyridinium Derivatives with 1,4-Dihydropyridines Enabled by Photoinduced Charge Transfer
Author(s)
Inwon Kim; Seongjin Park; Sunwoo Hong
Publication Date
2020-11
Journal
ORGANIC LETTERS, v.22, no.21, pp.8730 - 8734
Publisher
AMER CHEMICAL SOC
Abstract
© 2020 American Chemical Society. By exploiting electron donor-acceptor (EDA) complexes between 1,4-dihydropyridines and N-amidopyridinium salts under visible light irradiation, we discovered that photoinduced intermolecular charge transfer induces a single-electron transfer event without requiring a photocatalyst for the facile functionalization of pyridines. The generality of this method is amenable to various types of 1,4-dihydropyridines radical precursors to generate structurally different radicals such as alkyl, acyl, and carbamoyl radicals, ultimately providing facile access to synthetically valuable C4-functionalized pyridines. A broad range of functional groups are well accommodated under mild and metal-free conditions, and the synthetic utility of the present method is showcased by the late-stage functionalization of a variety of biologically relevant pyridine-based compounds, pharmaceuticals, and peptide feedstocks
URI
https://pr.ibs.re.kr/handle/8788114/7548
DOI
10.1021/acs.orglett.0c03347
ISSN
1523-7060
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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