Selective tetrahydropyranylation of alcohols and phenols using titanium(IV) salophen trifluoromethanesulfonate as an efficient catalyst

Abstract

Titanium(IV) salophen trifluoromethanesulfonate, [TiIV(salophen)(OSO2CF3)2], as a catalyst enables selective tetrahydropyranylation of alcohols and phenols with 3,4-dihydro-2H-pyran. Using this catalytic system, primary, secondary and tertiary alcohols, as well as phenols, were converted to their corresponding tetrahydropyranyl ethers in high yields and short reaction times at room temperature. Investigation of the chemoselectivity of this method showed discrimination between the activity of primary alcohols in the presence of secondary and tertiary alcohols and phenols. This heterogenized catalyst could be reused several times without loss of its catalytic activity. Copyright © 2016 John Wiley & Sons, Ltd. Copyright © 2016 John Wiley & Sons, Ltd.