Regioselective Benzylation of Diols and Polyols by Catalytic Amounts of an Organotin Reagent

An efficient one-pot method for the selective benzylation of diols and polyols using 0.1equiv. of organotin reagents and tetrabutylammonium bromide as catalyst has been developed. The diols and polyols containing a cis-vicinal diol were regioselectively benzylated in 70-94% isolated yields. A catalytic reaction mechanism was also proposed.