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Radical C−N Borylation of Aromatic Amines Enabled by a Pyrylium Reagent

MPS-Authors
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Ma,  Yuanhong
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Pang,  Yue
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Niski,  Jan
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Leutzsch,  Markus
Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Cornella,  Josep
Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Ma, Y., Pang, Y., Chabbra, S., Reijerse, E. J., Schnegg, A., Niski, J., et al. (2020). Radical C−N Borylation of Aromatic Amines Enabled by a Pyrylium Reagent. Chemistry – A European Journal, 26(17), 3738-3743. doi:10.1002/chem.202000412.


Cite as: http://hdl.handle.net/21.11116/0000-0006-4A2E-5
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.