title: Electrophilic trifluoromethylation of carbonyl compounds and their nitrogen derivatives under copper catalysis.
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.
authors.affiliation: Université Claude Bernard Lyon 1, CNRS UMR 5246, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, CPE Lyon, 43 Boulevard du 11 Novembre 1918, 69622-Villeurbanne, France. didier.bouyssi@univ-lyon1.fr nuno.monteiro@univ-lyon1.fr.
authors.forename: Alexis
authors.initials: A
authors.lastname: Prieto
authors.affiliation: University of Basel, Department of Chemistry, St. Johanns-Ring 19, CH-4056 Basel, Switzerland.
authors.forename: Olivier
authors.initials: O
authors.lastname: Baudoin
authors.affiliation: Université Claude Bernard Lyon 1, CNRS UMR 5246, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, CPE Lyon, 43 Boulevard du 11 Novembre 1918, 69622-Villeurbanne, France. didier.bouyssi@univ-lyon1.fr nuno.monteiro@univ-lyon1.fr.
authors.forename: Didier
authors.initials: D
authors.lastname: Bouyssi
authors.affiliation: Université Claude Bernard Lyon 1, CNRS UMR 5246, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, CPE Lyon, 43 Boulevard du 11 Novembre 1918, 69622-Villeurbanne, France. didier.bouyssi@univ-lyon1.fr nuno.monteiro@univ-lyon1.fr.
authors.forename: Nuno
authors.initials: N
authors.lastname: Monteiro