4.8 Article

Ligand-Controlled Ni(0)-Al(III) Bimetal-Catalyzed C3-H Alkenylation of 2-Pyridones by Reversing Conventional Selectivity

Journal

ACS CATALYSIS
Volume 11, Issue 8, Pages 4606-4612

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.1c00750

Keywords

nickel; aluminum; site-selective; 2-pyridone; alkenylation

Funding

  1. National Natural Science Foundation of China [91856104, 21871145, 21672107]
  2. Postdoctoral Science Foundation of China [2018M641625]
  3. Tianjin Applied Basic Research Project [19JCZDJC37900]
  4. Fundamental Research Funds for the Central Universities [63191601]
  5. Department of Education of Guangdong Province [2016KCXTD005, 2017KSYS010, 2019KZDXM035]
  6. Cutting-Edge Technology Research Plan [19JCZDJC37900]

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Conventional C-H alkenylation of 2-pyridone with electron-deficient C-H bonds typically occurs at the C6 or C4 position using low-valent transition-metal catalysis. However, a Ni-Al bimetallic catalyst with a bifunctional ligand resulted in a reversed selectivity, providing high yields of C3-alkenylated 2-pyridones.
Conventional C-H alkenylation with alkynes via low-valent transition-metal catalysis occurs at the C6 or C4 position of 2-pyridone with electron-deficient C-H bonds. A bifunctional ligand-bonded Ni-Al bimetallic catalyst resulted in a reversed selectivity, providing a series of C3-alkenylated 2-pyridones in up to 99% yields.

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