Visible-Light-Mediated Generation of Nitrogen-Radicals: Novel Amino-Functionalization Processes

Nitrogen-containing compounds are a privileged class of molecules, which have applications in medicines, agrochemicals, dyes and materials. As a result, the construction of C–N bonds is an extremely active area of research. Nitrogen-centered radicals are a versatile class of intermediates however, the difficulties associated with their generation have significantly thwarted their use in synthetic chemistry. Photoredox catalysis has emerged as a powerful technique through which single electron transfer reactions can be performed under mild conditions.

We have accomplished the formation and use of iminyl, amidyl and aminyl radicals in novel aminofunctionalization reactions through the design of a new class of reactive O-aryl oximes, hydroxyamides and hydroxylamines. Owing to their low reduction potentials, the inexpensive organic dye eosin Y could be used as the photoredox catalyst.