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Annulation of CF3-Imidoyl Sulfoxonium Ylides with 1,3-Dicarbonyl Compounds: Access to 1,2,3-Trisubstituted 5-Trifluoromethylpyrroles.

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A lithium-bromide-promoted nucleophilic substitution/annulation cascade reaction between CF3-imidoyl sulfoxonium ylides and 1,3-dicarbonyl compounds has been established, and the corresponding 1,2,3-trisubstituted 5-trifluoromethylpyrroles have been obtained in 27-78% yield. This reaction features… Click to show full abstract

A lithium-bromide-promoted nucleophilic substitution/annulation cascade reaction between CF3-imidoyl sulfoxonium ylides and 1,3-dicarbonyl compounds has been established, and the corresponding 1,2,3-trisubstituted 5-trifluoromethylpyrroles have been obtained in 27-78% yield. This reaction features a broad substrate scope and generates dimethyl sulfoxide and H2O as byproducts.

Keywords: trisubstituted trifluoromethylpyrroles; cf3 imidoyl; imidoyl sulfoxonium; dicarbonyl compounds; sulfoxonium ylides; ylides dicarbonyl

Journal Title: Organic letters
Year Published: 2021

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