Comptes Rendus Chimie p. 1095 - 1102 (2011)
Update date:2022-08-04
Topics:
Abdolmanaf Taghavi
Moghadam, Majid
Mohammadpoor-Baltork, Iraj
Tangestaninejad, Shahram
Mirkhani, Valiollah
Khosropour, Ahmad Reza
In the present work, the catalytic activity of high-valent tetraphenylporphyrinatovanadium(IV) trifluoromethanesulfonate, [V IV(TPP)(OTf)2], in the tetrahydropyranylation of alcohols and phenols with 3,4-dihydro-2H-pyran (DHP) is reported. This new electron-deficient V(IV) compound was used as a highly efficient catalyst for pyranylation of primary (aliphatic and benzylic), sterically-hindered secondary and tertiary alcohols with DHP. Tetrahydropyranylation of phenols with DHP was also performed to afford the desired THP-ethers. The chemoselectivity of this method was also investigated. The results indicated that primary alcohols are more reactive in the presence of secondary and tertiary alcohols and phenols. This catalyst was reused several times without loss of its activity.
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