In analogy to the classical reaction of C-B bonds with peroxides, the first oxidative functionalization of aminoboranes through a 1,2-N migration was realized. Readily available aliphatic nitro compounds are thereby transformed into N- and O-functionalized hydroxylamines in a single synthetic operation. Addition of hazardous peroxides is avoided. Instead, the insertion of O , as the terminal oxidant, into Zn-C bonds provides the necessary peroxides. The required zinc organyls, in turn, are formed through a boron-to-zinc exchange, from an organoboronic ester byproduct of the nitro-to-aminoborane transformation.

In analogy to the classical reaction of CÀBb onds with peroxides,t he first oxidative functionalization of aminoboranes through a1 ,2-N migration was realized.R eadily available aliphatic nitro compounds are thereby transformed into N-and O-functionalized hydroxylamines in as ingle synthetic operation. Addition of hazardous peroxides is avoided. Instead, the insertion of O 2 ,a st he terminal oxidant, into Zn À Cb onds provides the necessary peroxides.T he required zinc organyls,i nt urn, are formed through ab oronto-zinc exchange,f rom an organoboronic ester byproduct of the nitro-to-aminoborane transformation.Scheme 1. Oxidation of organoboranes (a) and aminoboranes (b).