Highly efficient and selective acetylation of alcohols and phenols with acetic anhydride catalyzed by a high-valent tin(IV) porphyrin, Sn(TPP)(BF4)2

Rapid and efficient acetylation of alcohols and phenols with acetic anhydride in the presence of tin(IV) tetraphenylporphyrinato tetrafluoroborate, SnIV(tpp)(BF4)2, as catalyst is reported. The high catalytic activity of this electron-deficient tin(IV) porphyrin can be used to assist the acetylation of not only primary alcohols but also sterically hindered secondary and tertiary alcohols with acetic anhydride. Acetylation of phenols with acetic anhydride was achieved to afford the desired esters efficiently. This catalyst selectively acetylates the alcohols and phenols in the presence of acetals and silyl ethers.

Figure optionsDownload as PowerPoint slide