Oxorhenium-catalyzed deoxydehydration of glycols and epoxides

Davis, Jacqkis; Srivastava, R. S.

doi:10.1016/j.tetlet.2014.05.044

Cited by 24 publications

(18 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[16,21,20,27] Because the substrate, main product, and active element of our system are similar to those of CH 3 ReO 3 -catalyzed deoxydehydration, the key steps can be similar in both systems. The proposed mechanism for simultaneous hydrodeoxygenation over ReO x -Pd/CeO 2 catalyst is shown in Scheme 2.…”

mentioning

confidence: 98%

“…3) These systems typically use other reductants than H 2 and lower yields are obtained if H 2 is used as the reductant. [16,20] Simultaneous hydrodeoxygenation of straightchain vicinal diols over heterogeneous Re catalysts has been reported; however, the yields of alkenes ( % 50 %) were lower than those obtained with homogeneous catalysts ( % 95 %), and the TON and TOF per Re atom were very low (< 20 and < 5 h À1 , respectively; Table S1, entries [27][28][29][30]. [27,28] In addition, there are no reports on the reuse of heterogeneous catalysts for deoxydehydration without decrease in activity up to now.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Hydrodeoxygenation of Vicinal OH Groups over Heterogeneous Rhenium Catalyst Promoted by Palladium and Ceria Support

et al. 2014

View full text Add to dashboard Cite

Heterogeneous ReO x -Pd/CeO 2 catalyst showed excellent performance for simultaneous hydrodeoxygenation of vicinal OH groups. High yield (> 99 %), turnover frequency (300 h À1 ), and turnover number (10 000) are achieved in the reaction of 1,4-anhydroerythritol to tetrahydrofuran. This catalyst can be applied to sugar alcohols, and mono-alcohols and diols are obtained in high yields (! 85 %) from substrates with even and odd numbers of OH groups, respectively. The high catalytic performance of ReO x -Pd/CeO 2 can be assigned to rhenium species with + 4 or + 5 valence state, and the formation of this species is promoted by H 2 /Pd and the ceria support.

show abstract

mentioning

confidence: 98%

mentioning

confidence: 99%

Hydrodeoxygenation of Vicinal OH Groups over Heterogeneous Rhenium Catalyst Promoted by Palladium and Ceria Support

et al. 2014

View full text Add to dashboard Cite

show abstract

“…[13] However, it is much more difficult to selectively remove OH groups with these catalysts from substrates with four or more OH groups such as erythritol, xylitol, and sorbitol. [15][16][17][18][19][20][21][22][23][24][25] In combination with the hydrogenation of the produced alkene, deoxydehydration transforms two vicinal OH groups to H atoms, and the reaction can be regarded as simultaneous hydrodeoxygenation (Scheme 1). On the other hand, Re, V, and Mo homogeneous catalysts, especially Re, have been reported to be active in deoxydehydration (didehydroxylation) of vicinal OH groups to give alkenes.…”

mentioning

confidence: 99%

“…1400; [16] TOF: max. [16,20] Simultaneous hydrodeoxygenation of straightchain vicinal diols over heterogeneous Re catalysts has been reported; however, the yields of alkenes ( % 50 %) were lower than those obtained with homogeneous catalysts ( % 95 %), and the TON and TOF per Re atom were very low (< 20 and < 5 h À1 , respectively; Table S1, entries [27][28][29][30]. 3) These systems typically use other reductants than H 2 and lower yields are obtained if H 2 is used as the reductant.…”

mentioning

confidence: 99%

Hydrodeoxygenation of Vicinal OH Groups over Heterogeneous Rhenium Catalyst Promoted by Palladium and Ceria Support

et al. 2014

View full text Add to dashboard Cite

show abstract

“…[152][153][154][155][156] Even in the recent literature, high temperatures and pressures were applied for conversion of styrene oxide to styrene to achieve better reaction efficiency. 157,158 The proposed mechanism for the selective reduction of epoxide is also illustrated in Scheme 6. The reduction was conducted in isopropanol solvent (also the hydrogen donor), and the species with the hydrogen atom bonded to the Au NP surface possible to form and react with the epoxide molecules on the Au NPs.…”

Section: Deoxygenation Of Epoxidesmentioning

confidence: 99%

Pd and Pd Based Alloy Nanoparticles as Visible Light Photocatalysts for Coupling Reactions under Ambient Conditions

Peiris¹

View full text Add to dashboard Cite

Photocatalysis is a rapidly emerging research field, with great potential for a wide range of applications, since it can utilize solar energy. Solar light has received much attention as it is the most abundant and cleanest renewable energy source, which produces no pollution. Therefore, synthesis of fine chemicals with solar light at ambient temperature is of the utmost interest. Nonetheless, it is still a challenge to devise new catalysts, which exhibit high activity under the full solar spectrum and moderate conditions. This project aimed to develop novel metal nanoparticle photocatalysts for several important organic reactions under visible light irradiation.The prospect of visible light irradiation driving chemical synthesis may extend the scope of organic synthesis via a more controlled, simplified, and greener process.Firstly, we focused on a systematic study of palladium nanoparticle-catalysed cross-coupling and homo-coupling reactions under visible light irradiation. These metal nanoparticles strongly absorb the light primarily through interband electronic transitions. The excited electrons interact with the reactant molecules adsorbed on the metal particle surface to accelerate coupling reactions. Therefore, the rate of the catalysed reaction depends on the concentration and energy of the excited electrons, which can be increased by increasing the light intensity. Nevertheless, mild reaction conditions, such as ambient temperatures and pressures in the reaction systems make it more environmentally benign.Secondly, we incorporated palladium metal component with silver nanoparticles to obtain silver-palladium alloy nanoparticles (Ag-Pd alloy NPs): which can catalyse the reductive coupling of nitroarenes reactions by light irradiation at ambient conditions. This provided a general indication for the possibility of the design of an alloy nanoparticle photocatalysts using silver with other transition metals, such as nickel, cobalt. This photocatalytic process is a more efficient and greener approach than thermal reactions for the reductive coupling of nitroarenes, and this improving the product yield by avoiding over-reduced products. The alloy nanoparticles strongly absorb light, energizing the conduction electrons of silver, which migrate to palladium sites at the alloy nanoparticle surface because of charge redistribution between the two metals. The alloying affects the charge redistribution iv between silver and palladium, which enhances interaction between reactant molecules and the nanoparticles. The reduction activity is sensitive to the intensity of the irradiation, the wavelength of the incident light, metal molar ratio and atmosphere of the reaction. When the molar ratio of silver and palladium in alloy nanoparticles is nearly equal, the catalysts exhibited the best performance.Finally, supported gold-palladium alloy nanoparticles (Au-Pd alloy NPs) on zirconium dioxide (ZrO 2 ) can act as efficient visible light photocatalysts for reductive N-alkylation of nitrobenzene with benzyl alcohol. ...

show abstract

Oxorhenium-catalyzed deoxydehydration of glycols and epoxides

Cited by 24 publications

References 24 publications

Hydrodeoxygenation of Vicinal OH Groups over Heterogeneous Rhenium Catalyst Promoted by Palladium and Ceria Support

Hydrodeoxygenation of Vicinal OH Groups over Heterogeneous Rhenium Catalyst Promoted by Palladium and Ceria Support

Hydrodeoxygenation of Vicinal OH Groups over Heterogeneous Rhenium Catalyst Promoted by Palladium and Ceria Support

Pd and Pd Based Alloy Nanoparticles as Visible Light Photocatalysts for Coupling Reactions under Ambient Conditions

Contact Info

Product

Resources

About