Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 143, Issue 32, Pages 12460-12466Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c06036
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Funding
- National Natural Science Foundation of China [22031008, 21801195]
- Science Foundation of Wuhan [2020010601012192]
- China Postdoctoral Science Foundation [2018M632906, 2019T120678]
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The paper presents an electrochemical palladium-catalyzed method for oxidative carbonylation, avoiding the hazardous mixing of CO with oxygen. This approach provides a diverse array of ynones and can serve as an alternative to the carbonylative Sonogashira reaction.
Oxidative carbonylation using carbon monoxide has evolved as an attractive tool to valuable carbonyl-containing compounds, while mixing CO with a stoichiometric amount of a chemical oxidant especially oxygen is hazardous and limits its application in scale-up synthesis. By employing anodic oxidation, we developed an electrochemical palladium-catalyzed oxidative carbonylation of arylhydrazines with alkynes, which is regarded as an alternative supplement of the carbonylative Sonogashira reaction. Combining an undivided cell with constant current mode, oxygen-free conditions avoids the explosion hazard of CO. A diversity of ynones are efficiently obtained using accessible arylhydrazines and alkynes under copper-free conditions. A possible mechanism of the electrochemical Pd(0)/Pd(II) cycle is rationalized based upon cyclic voltammetry, kinetic studies, and intermediates experiments.
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