Nitrogen atom

Catalysis

Photochemistry

Electrophile

Reactive intermediate

Heteroatom

Combinatorial chemistry

Organic chemistry

Photoredox catalysis

Nucleophile

Deoxygenation

Radical

Chemistry

Photocatalysis

Group (periodic table)

Ring (chemistry)

Copper

Organic Letters

A 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.

Photocatalytic Oxyamination of Alkenes: Copper(II) Salts as Terminal Oxidants in Photoredox Catalysis