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

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.

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 Creators:
Ma, Yuanhong1, Author              
Pang, Yue1, Author              
Niski, Jan1, Author              
Leutzsch, Markus2, Author              
Cornella, Josep1, Author              
Affiliations:
1Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2466693              
2Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445623              

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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.

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Language(s): eng - English
 Dates: 2019-11-262019-12-02
 Publication Status: Published online
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: No review
 Identifiers: DOI: 10.26434/chemrxiv.11211245.v1
 Degree: -

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Title: ChemRxiv
Source Genre: Commentary
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Publ. Info: American Chemical Society (ACS), Chinese Chemical Society, Chemical Society of Japan, German Chemical Society (GDCh), Royal Society of Chemistry
Pages: - Volume / Issue: - Sequence Number: - Start / End Page: - Identifier: -