Synthetic Chameleon Turns into Oximes, Nitrones, and Hydroxylamines when Exposed to Blue Light

A metal-free, user-friendly
photochemical transformation
of nitroalkanes
to oximes, nitrones, and hydroxylamines has been developed. The visible-light-induced
reactions are catalyzed by the readily available photoredox organocatalyst
4CzIPN and use inexpensive amines as reductants. Broad in scope and
tolerant of multiple functional groups and heterocycles, the transformation
proceeds under mild conditions. Its synthetic potential was demonstrated
in the formal total synthesis of amathaspiramide F. A basic insight
into the reaction mechanism was gained with the help of an NMR study.