Arenes with nitrogen-based functionalities are common and versatile building blocks used in synthetic organic chemistry in general and for pharmaceuticals in specific. The reactivity of nitrosoarenes is, in many cases, very different from the corresponding anilines and nitroarenes. This unique reactivity and selectivity can be utilized for the selective synthesis of a broad range of nitrogen-functionalized arenes. We report on two protocols for the selective synthesis of functionalized anilines, hydroxylamines, nitrosoarenes and nitroarenes from nitrosoarenes. The first protocol involves a copper-mediated para-selective halogenation of nitrosoarenes, yielding brominated or chlorinated nitrosoarenes, nitroarenes or anilines. The second protocol employs the Langlois reagent (sodium triflinate) for the selective addition of a CF3-radical to the nitrogen atom of nitrosoarenes, yielding CF3-substituted hydroxylamines. Both protocols tolerate a broad range of functional groups, display high regio- or chemo-selectivity and are easy to execute.

Nitrosoarenes as building blocks for nitrogen-functionalized arenes

253rd National Meeting (2017)

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