Daria V. Vorobyeva

Metal-carbenoid mediated CH-functionalization of pyrroles with methyl 2-diazo-3,3,3-trifluoropropionate

Metal-catalyzed CH-functionalization of pyrrole and its derivatives via insertion of CF3-carbene generated from methyl 2-diazo-3,3,3-trifluoropropionate was studied. The reactions are completed within few minutes upon heating in toluene in the presence of 1 mol.% of commercially available copper trifluoroacetylacetonate. These reaction conditions allow simultaneous introduction of trifluoromethyl and methyl carboxylate groups into the aromatic pyrrole ring. Conditions for C(2)-selective monofunctionalization of NH-pyrroles were developed.

Methyl 3,3,3-trifluoro-2-diazopropionate for the synthesis of functionalized styrenes

The efficient method for the synthesis of novel trifluoromethyl-containing hydroxy- and aminostyrenes has been developed. The reaction sequence includes the selective insertion of CF3-substituted carbene, which was catalytically derived from methyl 3,3,3-trifluoro-2-diazopropionate, into the OH- or NH-bonds of easily available o-bromophenol and o-bromoaniline derivatives followed by a bromine substitution for vinyl group via Pd-catalyzed Stille reaction.

Trifluoromethylated 5-aminoderivatives of (indol-3-yl)acetic acid

New CF3-containing derivatives of (5-aminoindol-3-yl)acetic acid were synthesized from 5-nitroindole and trifluoropyruvate or 2-diazotrifluoropropionate. Their reactions with isocyanates allowed us to obtain the series of new ureas, including sulfonylureas, containing a pharmacophore moiety of α-(trifluoromethyl)indolylacetic acid.