Direct Arylation of α‐Amino C(sp3)‐H Bonds by Convergent Paired Electrolysis

A metal‐free convergent paired electrolysis strategy to synthesize benzylic amines through direct arylation of tertiary amines and benzonitrile derivatives at room temperature has been developed. This TEMPO‐mediated electrocatalytic reaction makes full use of both anodic oxidation and cathodic reduc...

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Bibliographic Details
Published in:Angewandte Chemie 2019-11, Vol.131 (46), p.16700-16552
Main Authors: Ma, Yueyue, Yao, Xiantong, Zhang, Lei, Ni, Pufan, Cheng, Ruihua, Ye, Jinxing
Format: Article
Language:English
Subjects:
Amines
Anodizing
Arylierung
Benzonitrile
C-H-Aktivierung
Chemistry
Convergence
Electrolysis
Elektrokatalyse
Kreuzkupplung
Metals
Oxidants
Oxidation
Oxidizing agents
Room temperature
Tertiäre Amine
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Summary:A metal‐free convergent paired electrolysis strategy to synthesize benzylic amines through direct arylation of tertiary amines and benzonitrile derivatives at room temperature has been developed. This TEMPO‐mediated electrocatalytic reaction makes full use of both anodic oxidation and cathodic reduction without metals or stoichiometric oxidants, thus showing great potential and advantages for practical synthesis. This convergent paired electrolysis method provides a straightforward and powerful means to activate C−H bonds and realize cross‐coupling with cathodically generated species. Elektrisierend! Eine konvergente Elektrolysemethode liefert Benzylamine durch direkte Arylierung von tertiären Aminen und Benzonitrilderivaten ohne die Erfordernis stöchiometrischer Mengen von Oxidationsmitteln oder Metallen. Dieser elektrokatalytische Ansatz nutzt sowohl die Anoden‐ als auch die Kathodenreaktionen und bietet damit eine neue Perspektive zur elektrokatalytischen Kreuzkupplung anodisch und kathodisch generierter Reaktanten.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201909642