Journal
CHEMICAL COMMUNICATIONS
Volume 52, Issue 5, Pages 869-881Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5cc05954b
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- French Ministry of Higher Education and Research (MESR)
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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 alpha-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 alpha,beta-unsaturated ketones regioselectively incorporate the CF3 moiety at the alpha-position of the enones, trifluoromethylation occurs preferentially at the olefinic beta-carbon of the corresponding hydrazones.
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