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

preprint
submitted on 26.11.2019, 15:32 and posted on 02.12.2019, 08:30 by Yuanhong Ma, Yue Pang, jan niski, Markus Leutzsch, Josep Cornella
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.

Funding

Max Planck Gesellschaft

Max-Planck-Institut für Kohlenforschung

Fonds der Chemischen Industrie

History

Email Address of Submitting Author

cornella@kofo.mpg.de

Institution

Max-Planck-Institut für Kohlenforschung

Country

Germany

ORCID For Submitting Author

0000-0003-4152-7098

Declaration of Conflict of Interest

The authors declare no financial interest.

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in Chemistry – A European Journal

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