Investigation of catalytic activity of high-valent vanadium(IV) tetraphenylporphyrin: A new, highly efficient and reusable catalyst for acetylation of alcohols and phenols with acetic anhydride

In the present work, the catalytic activity of high-valent tetraphenylporphyrinatovanadium(IV) trifluoromethanesulfonate, [VIV(TPP)(OTf)2], in the acetylation of alcohols and phenols with Ac2O is reported. This new V(IV) catalyst was used as an efficient catalyst for not only primary alcohols (benzylic and aliphatic) but also sterically-hindered secondary and tertiary alcohols with acetic anhydride and the corresponding acetates were obtained in 85–99% yield and 0.5–15 min. Acetylation of phenols with acetic anhydride was also performed to afford the desired acetates in 88–99% and 1.5–20 min. This catalyst can be reused several times without loss of its catalytic activity.

Graphical abstractThe catalytic activity of high-valent [VIV(TPP)(OTf)2] in the acetylation of alcohols and phenols with Ac2O is reported. This new V(IV) catalyst was used as an efficient catalyst for not only primary alcohols but also sterically-hindered secondary and tertiary alcohols with acetic anhydride. Acetylation of phenols with acetic anhydride was also performed to afford the desired acetates. This catalyst can be reused several times without loss of its catalytic activity.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Electron-deficient V(IV) porphyrin was prepared and used as catalyst. ► Acetylation of alcohols and phenols with Ac2O was performed. ► The catalyst was reusable.