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

submitted on 26.05.2020, 16:42 and posted on 27.05.2020, 12:52 by Julia Duncan, Lun Li, Vahid Mohammadrezaei, Laina Geary
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.


Redefining the scope of the Pauson-Khand reaction vis-a-vis the origins of reactivity

National Institute of General Medical Sciences

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University of Nevada, Reno


United States

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