期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 59, 期 40, 页码 17511-17516出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202008435
关键词
aminopyridylation; bifunctional reagent; double umpolung; ketone; photocatalysis
资金
- Institute for Basic Science [IBS-R010-A2]
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.
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