cs7b01973_si_001.pdf (26.19 MB)
Aminomethylation of Aryl Halides Using α‑Silylamines Enabled by Ni/Photoredox Dual Catalysis
journal contribution
posted on 2017-08-16, 13:04 authored by Camille Remeur, Christopher B. Kelly, Niki R. Patel, Gary A. MolanderA 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.