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Issue 5, 2016
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Electrophilic trifluoromethylation of carbonyl compounds and their nitrogen derivatives under copper catalysis

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Abstract

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.

Graphical abstract: Electrophilic trifluoromethylation of carbonyl compounds and their nitrogen derivatives under copper catalysis

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Publication details

The article was received on 17 Jul 2015, accepted on 04 Nov 2015 and first published on 04 Nov 2015


Article type: Feature Article
DOI: 10.1039/C5CC05954B
Citation: Chem. Commun., 2016,52, 869-881
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    Electrophilic trifluoromethylation of carbonyl compounds and their nitrogen derivatives under copper catalysis

    A. Prieto, O. Baudoin, D. Bouyssi and N. Monteiro, Chem. Commun., 2016, 52, 869
    DOI: 10.1039/C5CC05954B

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