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Gold-Catalyzed, SN1-Type Reaction of Alcohols to Afford Ethers and Cbz-Protected Amines

Andrew R. S. Vinson, Victoria K. Davis, Arunamarie Arunasalam, Kate A. Jesse, Rachael E. Hamilton, Morgan A. Shattuck, Allison C. Hu, Robert G. Iafe, Anna G. Wenzel*

*Keck Science Department, Claremont McKenna, Pitzer and Scripps Colleges, 925 N. Mills Avenue, Claremont, CA 91711, USA, Email:

A. R. S. Vinson, V. K. Davis, A. Arunasalam, K. A. Jesse, R. E. Hamilton, M. A. Shattuck, A. C. Hu, R. G. Iafe, A. G. Wenzel, Synlett, 2015, 26, 765-770.

DOI: 10.1055/s-0034-1380128 (free Supporting Information)

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A gold-catalyzed, microwave protocol activates alcohols through an intermolecular, SN1-type reaction to directly form unsymmetrical ethers and Cbz-protected amines in good yields. This reaction is highly reproducible and tolerates moisture.

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Key Words

gold catalysis, microwave synthesis, ethers, amination, substitution

ID: J60-Y2015