Gold-Catalyzed, S_N1-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: awenzelkecksci.claremont.edu

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

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Abstract

A gold-catalyzed, microwave protocol activates alcohols through an intermolecular, S_N1-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

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ID: J60-Y2015