4.8 Article

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

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 46, Pages 16548-16552

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201909642

Keywords

arylation; cross-coupling; C-H activation; electrocatalysis; tertiary amines

Funding

  1. National Natural Science Foundation of China [21272068, 21572056]
  2. Program for New Century Excellent Talents in University [NCET-13-0800]
  3. Fundamental Research Funds for the Central Universities
  4. 111 project [B07023]
  5. Open Project of State Key Laboratory of Chemical Engineering [SKL-ChE-17C01]

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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.

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