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

preprint
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.

Funding

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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History

Email Address of Submitting Author

lgeary@unr.edu

Institution

University of Nevada, Reno

Country

United States

ORCID For Submitting Author

0000-0001-7511-4983

Declaration of Conflict of Interest

No conflict of interest

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