4.5 Article

Synthesis of Trifluoromethylated Dithiocarbamates via Photocatalyzed Substitution Reaction: Pentafluoropyridine as Activating Reagent

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2021, Issue 6, Pages 1007-1010

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202001572

Keywords

Dithiocarbamates; Fluorine; Photocatalysis; Radical reactions; Trifluoromethylation

Funding

  1. Russian Science Foundation [20-13-00112]
  2. Russian Science Foundation [20-13-00112] Funding Source: Russian Science Foundation

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The method involves nucleophilic trifluoromethylation, derivatization of the silyloxy group, and substitution of the fluorinated pyridinyloxy group, leading to the synthesis of trifluoromethyl-substituted dithiocarbamates.
A method for the synthesis of trifluoromethyl-substituted dithiocarbamates from aldehydes is described. The reaction involves nucleophilic trifluoromethylation, derivatization of the silyloxy-group with pentafluoropyridine, and substitution of the fluorinated pyridinyloxy group by dithiocarbamate anion. The substitution step is performed in the presence of 12-phenyl-12H-benzo[b]phenothiazine and copper cyanide under irradiation of 400 nm LED.

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