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Published on: May 21, 2019
Aminomethylation of Aryl Halides using α-Silylamines Enabled by Ni/Photoredox Dual Catalysis
Camille Remeur1, Christopher B Kelly1, Niki R Patel1
1Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323.
Abstract:
A protocol for the aminomethylation of aryl halides using α-silylamines via Ni/photoredox dual catalysis is described. The low oxidation potential of these silylated species enables facile single electron transfer (SET) oxidation of the amine followed by rapid desilylation. The resulting α-amino radicals can be directly funneled into a nickel-mediated cross-coupling cycle with aryl halides. The process accomplishes aminomethylation under remarkably mild conditions and tolerates numerous aryl- and heteroaryl halides with an array of functional groups.
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