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Photocatalytic Vicinal Aminopyridylation of Methyl Ketones by a Double Umpolung Strategy

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Title
Photocatalytic Vicinal Aminopyridylation of Methyl Ketones by a Double Umpolung Strategy
Author(s)
Honggu Im; Wonjun Choi; Sungwoo Hong
Subject
aminopyridylation, ; bifunctional reagent, ; double umpolung, ; ketone, ; photocatalysis
Publication Date
2020-09
Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.59, no.40, pp.17511 - 17516
Publisher
WILEY-V C H VERLAG GMBH
Abstract
© 2020 Wiley-VCH GmbHA photocatalytic double umpolung strategy for the vicinal aminopyridylation of ketones was developed using pyridinium N−N ylides. The inversion of the polarity of the pyridinium N−N ylides by single-electron oxidation successfully enables radical-mediated 1,3-dipolar cycloadditions with enolsilanes formed in situ from ketones, followed by homolytic cleavage of the N−N bond. Intriguingly, the nucleophilic amino and electrophilic pyridyl groups in the ylides can be installed at the nucleophilic α-position and electrophilic carbonyl carbon, respectively, which are typically inaccessible by their innate polarity-driven reactivity. This method accommodates a broad scope, and the utility was further demonstrated by the late-stage functionalization of complex biorelevant molecules. Moreover, the strategy can be successfully applied to enamides
URI
https://pr.ibs.re.kr/handle/8788114/7658
DOI
10.1002/ange.202008435
ISSN
1433-7851
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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