Organic Synthesis “On Water”

Chanda, Arani; Fokin, Valery V.

doi:10.1021/cr800448q

Cited by 1,365 publications

(567 citation statements)

References 168 publications

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“…It is known that water is an interesting promoter for organic synthetic reactions and an explanation for the promotional effects observed is hydrogen bonding that could occur at the organic (substrate) -aqueous interface but not in the bulk. Such promoted reactions are refereed to as on-water reactions [11,12]. Most of on-water reactions reported are homogeneous synthetic reactions including molecular catalysts and no gaseous reactants.…”

mentioning

confidence: 99%

Multiphase reaction media including dense phase carbon dioxide and/or water: A case study for hydrogenation of phenol with a Pd/Al2O3 catalyst

Yoshida

Narisawa

Fujita

et al. 2013

Journal of Molecular Catalysis A: Chemical

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Multiphase reaction media including dense phase CO 2 and/or water were applied for a test reaction of hydrogenation of phenol with a Pd/Al 2 O 3 catalyst. The features of these reaction media were clarified and the actions of dense phase CO 2 and water were discussed. Different characterization methods (XPS, in situ high pressure FTIR, ICP) were used to study (i) the surface of supported Pd particles that varied during the reaction, (ii) the competitive adsorption of phenol, water, and CO that was formed from H 2 and CO 2 under pressurized conditions, and (iii) the leaching of active Pd species. Dense phase CO 2 caused the deactivation of catalyst and it 2 occurred more rapidly in the presence of both dense phase CO 2 and water. In the system including water alone, the catalyst deactivation also happened but gradually. At the latter stage of reaction in this system, phenol was not consumed but cyclohexanone did transform to cyclohexanol. Those results may be explained by the leaching of Pd species and a structural change of supported Pd particles, resulting in a change in their adsorption behavior. The Pd leaching is more significant in acidic aqueous phase dissolving CO 2 at high pressure.

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mentioning

confidence: 99%

Multiphase reaction media including dense phase carbon dioxide and/or water: A case study for hydrogenation of phenol with a Pd/Al2O3 catalyst

Yoshida

Narisawa

Fujita

et al. 2013

Journal of Molecular Catalysis A: Chemical

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“…Recently, organic synthesis on water has also been reviewed by Fokin and co-workers. 17 Based on their study, it would appear that this reaction type may be placed in the category of ' on-water ' synthetic reactions.…”

Section: Resultsmentioning

confidence: 99%

A facile and practical p-Toluenesulfonic acid catalyzed route to dicoumarols containing an Aroyl group

et al. 2015

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New and known dicoumarols may be efficiently synthesized employing p-toluenesulfonic acid (p-TSA) as a solid acid catalyst from the reaction of 4-hydroxycoumarin with aryl glyoxal in water. This method offers direct access to structurally diverse coumarin derivatives in moderate to good yields (up to 65%). A total of five new compounds were synthesized. KEYWORDSDicoumarol, p-toluenesulfonic acid, aryl glyoxal, 4-hydroxycoumarin.

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“…With this concern, use of water has attracted much attention [6][7][8][9][10][11], however water based processes are still subject to limitations due to solubility problems of highly hydrophobic substrates. On the other hand, excellent solvent properties like low toxicity (LD50 (oral rat) 12600 mg/kg), biodegradability, low-flammability, long liquid range (Boiling point 290 °C), low vapor pressure and solubility of polar organic compounds made the glycerol an excellent option to use as solvent for organic synthesis [12].…”

Section: Introductionmentioning

confidence: 99%

Glycerol mediated, one pot, multicomponent synthesis of dihydropyrano[2,3-c]pyrazoles

Sohal¹,

Goyal²,

Sharma³

et al. 2013

Eur. J. Chem.

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Organic Synthesis “On Water”

Cited by 1,365 publications

References 168 publications

Multiphase reaction media including dense phase carbon dioxide and/or water: A case study for hydrogenation of phenol with a Pd/Al2O3 catalyst

Multiphase reaction media including dense phase carbon dioxide and/or water: A case study for hydrogenation of phenol with a Pd/Al2O3 catalyst

A facile and practical p-Toluenesulfonic acid catalyzed route to dicoumarols containing an Aroyl group

Glycerol mediated, one pot, multicomponent synthesis of dihydropyrano[2,3-c]pyrazoles

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