Metal-carbenoid mediated CH-functionalization of pyrroles with methyl 2-diazo-3,3,3-trifluoropropionate |
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| Authors: | I E Iagafarova D V Vorobyeva A V Krishtalovich A S Peregudov S N Osipov |
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| Institution: | 1.A. N. Nesmeyanov Institute of Organoelement Compounds,Russian Academy of Sciences,Moscow,Russian Federation;2.N. D. Zelinsky Institute of Organic Chemistry,Russian Academy of Sciences,Moscow,Russian Federation |
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| Abstract: | 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. |
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