Rapid transformation of benzylic alcohols to aldehyde in the presence of cucurbit[8]uril

Heterogeneous catalytic oxidation of veratryl alcohol to veratryaldehyde with o-iodoxybenzoic acid (IBX) in the presence of cucurbit[8]uril (Q[8]) has been investigated. The evidence of oxidation kinetics affirmed the supramolecular catalysis of Q[8]. Experimental investigation of addition of catalyst and the initial pH suggested that the optimum proportion of reagents is a 0.1:1:1 M ratio (Q[8]:alcohol:IBX) and neutral pH value. The screening of macrocycles, such as cucurbiturils and cyclodextrins, indicated the obvious dependence of catalytic activity on the cavity size and chemical structure of catalysts. The Q[8]-catalytic transformation of benzyl alcohol and 3-methoxybenzyl alcohol exhibited a very satisfying conversion.