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

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.

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Genre: Journal Article

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 Creators:
Ma, Yuanhong1, Author              
Pang, Yue1, Author              
Chabbra, Sonia2, Author
Reijerse, Edward J.2, Author
Schnegg, Alexander2, Author
Niski, Jan1, Author              
Leutzsch, Markus3, Author              
Cornella, Josep1, Author              
Affiliations:
1Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2466693              
2Max-Planck-Institut für Chemische Energiekonversion, Stiftstrasse 34–36, Mülheim an der Ruhr, 45470 Germany, ou_persistent22              
3Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445623              

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Free keywords: aromatic amine; C-N bond functionalization; pyridinium salts; pyrylium; radical borylation
 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: 2020-01-242020-01-292020-03-23
 Publication Status: Published in print
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/chem.202000412
 Degree: -

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Title: Chemistry – A European Journal
  Other : Chem. – Eur. J.
  Other : Chem. Eur. J.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 26 (17) Sequence Number: - Start / End Page: 3738 - 3743 Identifier: ISSN: 0947-6539
CoNE: https://pure.mpg.de/cone/journals/resource/954926979058