Regioselective α-Amination of Ethers Using Stable N-Chloroimides and Lithium tert-Butoxide.

Author(s) Gasonoo, M.; Thom, Z.W.; Laulhé, S.
Journal J Org Chem
Date Published 2019 Jul 05
Abstract

Herein we describe a metal-free regioselective α-amination of ethers mediated by N-chloroimides in ethereal solvents in the presence of lithium tert-butoxide. This reactivity of N-chloroimides leads to the synthesis of hemiaminal ethers in good to excellent yields at room temperature. This C-H functionalization is achieved without the use of a light, heat source, or external radical initiators. Initial mechanistic work indicates that the reaction proceeds through a radical pathway.

DOI 10.1021/acs.joc.9b00824
ISSN 1520-6904
Citation Gasonoo M, Thom ZW, Laulhé S. Regioselective α-Amination of Ethers Using Stable N-Chloroimides and Lithium tert-Butoxide. J Org Chem. 2019;84(13):8710-8716.

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