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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;

/persons/resource/persons243252

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., Niski, J., Leutzsch, M., & Cornella, J. (2019). Radical C‒N Borylation of Aromatic Amines Enabled by a Pyrylium Reagent. doi:10.26434/chemrxiv.11211245.v1.


Cite as: https://hdl.handle.net/21.11116/0000-0005-9EBD-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.