ol8b03345_si_001.pdf (8.27 MB)
Photocatalytic Oxyamination of Alkenes: Copper(II) Salts as Terminal Oxidants in Photoredox Catalysis
journal contribution
posted on 2018-11-08, 20:05 authored by Nicholas
L. Reed, Madeline I. Herman, Vladimir P. Miltchev, Tehshik P. YoonA photocatalytic
method for the oxyamination of alkenes using simple
nucleophilic nitrogen atom sources in place of prefunctionalized electrophilic
nitrogen atom donors is reported. Copper(II) is an inexpensive, practical,
and uniquely effective terminal oxidant for this process. In contrast
to oxygen, peroxides, and similar oxidants commonly utilized in non-photochemical
oxidative methods, the use of copper(II) as a terminal oxidant in
photoredox reactions avoids the formation of reactive heteroatom-centered
radical intermediates that can be incompatible with electron-rich
functional groups. As a demonstration of the generality of this concept,
it has been shown that diamination and deoxygenation reactions can
also be accomplished using similar photooxidative conditions.