Electrophilic trifluoromethylation of carbonyl compounds and their nitrogen derivatives under copper catalysis.

نویسندگان

  • Alexis Prieto
  • Olivier Baudoin
  • Didier Bouyssi
  • Nuno Monteiro
چکیده

Recent advances in electrophilic trifluoromethylation reactions of carbonyl compounds and their usual surrogates are highlighted with particular focus on copper-catalysed (or mediated) C-CF3 bond forming reactions. Ketones and aldehydes (notably via their enol ether and enamine derivatives) enable electrophilic trifluoromethylation at the α-carbon of the carbonyl compounds, whereas aldehyde N,N-disubstituted hydrazones undergo electrophilic attack of the cationic or radical CF3 species at the azomethine carbon, thus providing an umpolung alternative to nucleophilic trifluoromethylation of carbonyl compounds. A reversal in reactivity is also observed for conjugated systems. While α,β-unsaturated ketones regioselectively incorporate the CF3 moiety at the α-position of the enones, trifluoromethylation occurs preferentially at the olefinic β-carbon of the corresponding hydrazones.

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عنوان ژورنال:
  • Chemical communications

دوره 52 5  شماره 

صفحات  -

تاریخ انتشار 2016