Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 364, Issue 4, Pages 845-854Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202101361
Keywords
Electrochemical; Hydropyridylation; Ketone-activated alkenes; Insight into the mechanism
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Funding
- National Natural Science Foundation of China [21902083]
- Natural Science Foundation of Shandong Province [ZR2020QB130, ZR2021QB159]
- Talent Program Foundation of Qufu Normal University [6132, 6125]
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This work describes an electrochemical method for hydropyridylation of ketone-activated alkenes using ammonium cation, giving access to beta-pyridyl ketones. The method features a broad substrate scope and gram-scale synthesis, with ammonium chloride playing various roles in the transformation. Experiments and DFT calculations confirm the mechanism of dual proton-coupled electron transfer followed by radical cross-coupling as the preferred pathway.
This work describes an electrochemical ammonium cation enabled hydropyridylation of ketone-activated alkenes under metal- and exogenous reductant free conditions giving access to beta-pyridyl ketones, through dual proton-coupled electron transfer and radical cross-coupling. It features a broad substrate scope and allows a gram-scale synthesis. Ammonium chloride plays various roles in this transformation such as the hydrogen donor, the protonation reagent, and electrolyte. In particular, various experiments and density functional theory (DFT) calculation results show the mechanism of dual proton-coupled electron transfer followed by radical cross-coupling is the preferred pathway.
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