Oxidative Radical-Mediated Addition of Ethers to Quinone Imine Ketals: An Access to Hemiaminals.

J Org Chem

Chemical Engineering & Process Development Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India.

Published: February 2021

The highly regioselective synthesis of substituted hemiaminal addition of ethers to quinone imine ketals (QIKs) has been developed under metal-free conditions. In the presence of tetrabutylammonium chloride and potassium persulfate (KSO), QIKs couple efficiently with cyclic and acyclic ethers to give hemiaminals. This strategy offers an easy access to substituted hemiaminal ethers with high functional group tolerance in good to excellent yields.

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http://dx.doi.org/10.1021/acs.joc.0c02254DOI Listing

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