Scandium and Dimethylaminopyridine Catalyzed Dehydrative Coupling of Secondary Benzylic and Primary Alcohols to Synthesize Unsymmetrical Ethers

We developed a direct catalytic condensation of benzylic alcohols and primary alcohols to synthesize unsymmetrical ethers in one step, catalyzed by scandium triflate and p-dimethylaminopyridine (DMAP). Preliminary experiments give some insight into the mechanism of the reaction, though suggest that the process is quite complex. We suspect the rapid formation of a dimer from a secondary benzylic alcohol via a carbocation intermediate precedes unsymmetrical ether formation. Full experimental details and spectroscopic data are provided as supplementary information.