4.7 Article

Aqueous and Visible-Light-Promoted C-H (Hetero)arylation of Uracil Derivatives with Diazoniums

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 23, Pages 16434-16447

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01799

Keywords

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Funding

  1. National Key R&D Program of China [2017YFA0208100, 2020YFA0707901]
  2. National Natural Science Foundation of China [22022704, 91853124, 21977097, 21778057]
  3. Chinese Academy of Sciences

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The direct C5 (hetero)arylation of uracil and uridine substrates with (hetero)aryl diazonium salts under photoredox catalysis with blue light was reported. The coupling proceeds efficiently with good functional group tolerance at room temperature in aqueous solution without transition-metal components. A plausible radical mechanism has been proposed for this reaction.
Direct C5 (hetero)arylation of uracil and uridine substrates with (hetero)aryl diazonium salts under photoredox catalysis with blue light was reported. The coupling proceeds efficiently with diazonium salts and heterocycles in good functional group tolerance at room temperature in aqueous solution without transition-metal components. A plausible radical mechanism has been proposed.

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