Investigation of the catalytic activity of an electron-deficient vanadium(IV) tetraphenylporphyrin: A new, highly efficient and reusable catalyst for ring-opening of epoxides

In this work, the catalytic activity of high-valent tetraphenylporphyrinatovanadium(IV) trifluoromethanesulfonate, [VIV(TPP)(OTf)2], in the nucleophilic ring-opening of epoxides is reported. This new V(IV) catalyst was used as an efficient catalyst for alcoholysis with primary (methanol, ethanol and n-propanol), secondary (iso-propanol) and tertiary alcohols (tert-butanol), hydrolysis and acetolysis of epoxides with acetic acid and also for the conversion of epoxides to 1,2-diacetates with acetic anhydride, conversion of epoxides to thiiranes with ammonium thiocyanate and thiourea, and for conversion of epoxides to acetonides with acetone. The catalyst was reused several times without loss of its activity.

Graphical abstractThe catalytic activity of high-valent [VIV(TPP)(OTf)2] in the nucleophilic ring-opening of epoxides is reported. This new V(IV) catalyst has been used as an efficient catalyst for the alcoholysis, hydrolysis and acetolysis of epoxides, and also for the conversion of epoxides to 1,2-diacetates, thiiranes and acetonides. The catalyst was reused several times without loss of its activity.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► An electron-deficient V(IV) porphyrin was prepared and used as a catalyst. ► Ring-opening of epoxides were performed. ► The catalyst was reusable.