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Free keywords:
pyrylium radicals; aromatic amines; pyridinium cations; C-N bond activation; borylation reaction
Abstract:
Herein, we report a radical borylation of aromatic amines through a homolytic C(sp2)‒N bond cleavage. This method capitalizes on a simple and mild activation via a pyrylium reagent (ScPyry-OTf) thus priming the amino group for reactivity. The combination of terpyridine and a diboron reagent triggers a radical reaction which cleaves the C(sp2)‒N bond and forges a new C(sp2)‒B bond. The unique non-planar structure of the pyridinium intermediate, provides the necessary driving force for the aryl radical formation. The method permits borylation of a wide variety of aromatic amines indistinctively of the electronic environment.
