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Can Heteroarenes/Arenes Be Hydrogenated Over Catalytic Pd/C Under Ambient Conditions?
Author(s) -
Tanaka Nao,
Usuki Toyonobu
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000695
Subject(s) - chemistry , catalysis , steric effects , piperidine , pyridine , acetic acid , substrate (aquarium) , palladium , organic chemistry , solvent , density functional theory , medicinal chemistry , computational chemistry , photochemistry , combinatorial chemistry , oceanography , geology
Hydrogenation of over a dozen aromatic compounds, including both heteroarenes and arenes, over palladium on carbon (Pd/C, 1–100 mol%) with H 2 ‐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 the steric bulkiness of substituents. Moreover, the established method was used for the concise synthesis of the anti‐Alzheimer drug donepezil (Aricept®).