4.8 Article

Catalyst-free benzylic C(sp3)-H cross-coupling with organotrifluoroborates enabled by electrochemistry

Journal

GREEN CHEMISTRY
Volume 24, Issue 20, Pages 7883-7888

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2gc02204d

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Funding

  1. Key Project of the Provincial Natural Science Research Foundation of Anhui Universities, China [KJ2020A1195]
  2. National Science Foundation of China [21772061]
  3. Open Project of Key Laboratory of Green and Precise Synthetic Chemistry and Applications, Ministry of Education [2020KF02]
  4. National Undergraduate Innovation and Entrepreneurship Training Program [202110373003]
  5. Laboratory Open Project of Huaibei Normal University [2021sykf014]

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In this study, we report a rare catalyst-free electrochemical cross-coupling reaction that can forge various types of chemical bonds at room temperature. The study also reveals the dual role of organotrifluoroborates as both coupling partner and electrolyte in the C-H functionalization reaction.
Herein, we report a rare catalyst-free electrochemical cross-coupling of benzylic C-H bonds with organotrifluoroborates, which readily proceeds at room temperature and provides a unique protocol for forging C(sp(3))-C(sp(3)), C(sp(3))-C(sp(2)) and C(sp(3))-C(sp) bonds. In particular, this work discloses the dual role of organotrifluoroborates serving both as a coupling partner and an electrolyte in C(sp(3))-H functionalization.

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