An economic and efficient tetrahydrofuranylation of alcohols, imines and alkynes

The tetrahydrofuranyl radical, generated by heating tetrahydrofuran in the presence of air and allyl or benzyl chloride, becomes a useful tool in order to transform the hydroxyl functions into ethers, or the C=N double bond into amine, or the C-C triple bond into vinyl derivatives. A radical mechanism is proposed followed by a nucleophilic substitution for the alcohol substrate and a radical addition for the iminic and the acetylenic reactants. (C) 2010 Elsevier Ltd. All rights reserved.