Photocatalytic Vicinal Aminopyridylation of Methyl Ketones by a Double Umpolung Strategy

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A 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 alpha-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.
Publisher
WILEY-V C H VERLAG GMBH
Issue Date
2020-09
Language
English
Article Type
Article
Citation

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v.59, no.40, pp.17511 - 17516

ISSN
1433-7851
DOI
10.1002/anie.202008435
URI
http://hdl.handle.net/10203/276509
Appears in Collection
CH-Journal Papers(저널논문)
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