2020
DOI: 10.1002/ejoc.202000695
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Can Heteroarenes/Arenes Be Hydrogenated Over Catalytic Pd/C Under Ambient Conditions?

Abstract: Hydrogenation of over a dozen aromatic compounds, including both heteroarenes and arenes, over palladium on carbon (Pd/C, 1–100 mol%) with H2‐balloon pressure at room temperature is reported. Analyses using pyridine as a model substrate revealed that acetic acid was the best solvent, as using only 1 mol% Pd/C provided piperidine quantitatively. Substrate scope analysis and density functional theory calculations indicated that reaction rates are highly dependent on frontier molecular orbital characteristics and… Show more

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Cited by 30 publications
(23 citation statements)
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References 77 publications
(100 reference statements)
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“…Although the aryl group attached directly to the pyridine core could be sterically bulky, the loading of 20 mol% of Pd/C was sufficient to furnish the piperidine rings within the target compounds 4a ‐ c . The chemo‐selectivity of the hydrogenation in this work was not consistent with the previous report [7] where a pyridine‐type moiety could be completely reduced while a benzene‐type arene could persist under the reaction conditions. This selectivity can be accounted for by the frontier molecular orbital properties of the protonated aryl‐pyridines.…”
Section: Resultscontrasting
confidence: 80%
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“…Although the aryl group attached directly to the pyridine core could be sterically bulky, the loading of 20 mol% of Pd/C was sufficient to furnish the piperidine rings within the target compounds 4a ‐ c . The chemo‐selectivity of the hydrogenation in this work was not consistent with the previous report [7] where a pyridine‐type moiety could be completely reduced while a benzene‐type arene could persist under the reaction conditions. This selectivity can be accounted for by the frontier molecular orbital properties of the protonated aryl‐pyridines.…”
Section: Resultscontrasting
confidence: 80%
“…The reaction rate of the hydrogenation step is highly dependent on the electronic states of the pyridine rings as well as the positions and the steric hindrances of the substituents according to previous reports [7,10]. Although the aryl group attached directly to the pyridine core could be sterically bulky, the loading of 20 mol% of Pd/C was sufficient to furnish the piperidine rings within the target compounds 4a ‐ c .…”
Section: Resultsmentioning
confidence: 76%
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