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Visible-Light-Enabled Ortho-Selective Aminopyridylation of Alkenes with N-Aminopyridinium Ylides

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Title
Visible-Light-Enabled Ortho-Selective Aminopyridylation of Alkenes with N-Aminopyridinium Ylides
Author(s)
Yonghoon Moon; Wooseok Lee; Sungwoo Hong
Subject
C-H FUNCTIONALIZATION, ; PHOTOREDOX CATALYSIS, ; CYCLOADDITION REACTIONS, ; UNACTIVATED ALKENES, ; HYDROAMINATION, ; ALKYLATION, ; HETEROARYLATION, ; PYRIDYLATION, ; ALDEHYDES, ; REAGENTS
Publication Date
2020-07
Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.142, no.28, pp.12420 - 12429
Publisher
AMER CHEMICAL SOC
Abstract
© 2020 American Chemical Society.By utilizing an underexplored reactivity mode of N-aminopyridinium ylides, we developed the visible-light-induced ortho-selective aminopyridylation of alkenes via radical-mediated 1,3-dipolar cycloaddition. The photocatalyzed single-electron oxidation of N-aminopyridinium ylides generates the corresponding radical cations that enable previously inaccessible 1,3-cycloaddition with a broader range of alkene substrates. The resulting cycloaddition adducts rapidly undergo subsequent homolytic cleavage of the N-N bond, conferring a substantial thermodynamic driving force to yield various β-aminoethylpyridines. Remarkably, amino and pyridyl groups can be installed into both activated and unactivated alkenes with modular control of ortho-selectivity and 1,2-syn-diastereoselectivity under metal-free and mild conditions. Combined experimental and computational studies are conducted to clarify the detailed reaction mechanism and the origins of site selectivity and diastereoselectivity
URI
https://pr.ibs.re.kr/handle/8788114/7777
DOI
10.1021/jacs.0c05025
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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