Hydrierung aromatischer Verbindungen mit Platin und Wasserstoff

Willstätter, Richard; Hatt, Daniel

doi:10.1002/cber.19120450207

Cited by 51 publications

(16 citation statements)

References 9 publications

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“…Removal of a small amount of solvent was performed by Smart Evaporator CEV1-SQ-P2, CEV1-SK-P2, and CEV1A-GR-P2 (Kanagawa, Japan). 1 H and 13 C nuclear magnetic resonance (NMR) spectra were recorded on Bruker Avance III HD 400 spectrometer (400 MHz) or JEOL JNM-ECA 500 spectrometer (500 MHz). 1 H NMR data are reported as follows: chemical shift (δ, ppm), integration, multiplicity (s, singlet; d, doublet; t, triplet; q, quartet; m, multiplet), coupling constants (J) in Hz, assignments.…”

Section: Methodsmentioning

confidence: 99%

“…[32] The spectroscopic data werer compared with previously published data. [33] 3,5-Dimethylpiperidine Hydrochloride (2ab•HCl): 1 The spectroscopic data were compared with previously published data. [34] 2,6-Dimethylpiperidine Hydrochloride (2ac•HCl): 1 H NMR (500 MHz, CD 3 OD) δ = 1.40 (3H, J = 7.0, 3.0 Hz, Me), 1.32 (3H, dt, J = 6.5, 2.0 Hz, Me).…”

Section: Condition Bmentioning

confidence: 99%

“…The other signals could not be assigned unambiguously. [35] 4-Hydroxypiperidine Hydrochloride (2ae•HCl): 1 (m/z) calcd. for C 5 H 9 NO [M] 99.1, found 99.…”

Section: Condition Bmentioning

confidence: 99%

“…Hydrogenation of aromatic compounds is a powerful tool used in organic synthesis laboratories and the chemical industry for constructing alicyclic skeletons. Hydrogenation of aromatic rings was first achieved more than a century ago, [1] and since then, additional approaches to dearomatic hydrogenation as well as mechanistic studies have been reported. [2,3] In the past, these reactions were conducted using different metals under harsh conditions, such as high temperature and high pressure.…”

Section: Introductionmentioning

confidence: 99%

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Can Heteroarenes/Arenes Be Hydrogenated Over Catalytic Pd/C Under Ambient Conditions?

Tanaka

Usuki

2020

Eur J Org Chem

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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 the steric bulkiness of substituents. Moreover, the established method was used for the concise synthesis of the anti‐Alzheimer drug donepezil (Aricept®).

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Section: Methodsmentioning

confidence: 99%

Section: Condition Bmentioning

confidence: 99%

“…The other signals could not be assigned unambiguously. [35] 4-Hydroxypiperidine Hydrochloride (2ae•HCl): 1 (m/z) calcd. for C 5 H 9 NO [M] 99.1, found 99.…”

Section: Condition Bmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Can Heteroarenes/Arenes Be Hydrogenated Over Catalytic Pd/C Under Ambient Conditions?

Tanaka

Usuki

2020

Eur J Org Chem

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“…(188) In these cases it appears that the catalyst is poisoned by the pyrrole. In the absence of acid, hydrogénation of pyrroles in the liquid phase has been reported to proceed extremely slowly (182) and reports of vapour phase hydrogénation are relatively few. (183) In general, the hydrogénation of pyrroles has been conducted in acetic acid and ethanolic hydrochloric acid, but early workers reported low yields of pyrrolidines accompanied by extensive acid-catalyzed polymerization of the pyrrole.…”

Section: Catalytic Hydrogenationmentioning

confidence: 99%