Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 13, Pages 8710-8716Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b00824
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Funding
- Indiana Clinical and Translational Sciences Institute from the National Institutes of Health, National Center for Advancing Translational Sciences, Clinical and Translational Sciences Award [UL1TR002529]
- Indiana University Purdue University Indianapolis (IUPUI)
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Herein we describe a metal-free regioselective alpha-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.
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