Chemoselective Reduction of Complex α,β‐Unsaturated Ketones to Allylic Alcohols over Ir‐Metal Particles on β Zeolites

bruyn, Mario De; Coman, Simona M.; Bota, Roxana Melania; Pârvulescu, Vasile I.; Vos, Dirk De; Jacobs, Pierre

doi:10.1002/anie.200352275

Cited by 63 publications

(10 citation statements)

References 13 publications

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“…Of particular significance is that the reaction even proceeded smoothly in the presence of FA, with the FA remaining intact and therefore offering practical advantages in terms of the potential for the direct processing of a biomass-derived LA/FA solution. The Ir-based metal catalysts, which had previously been established to be prominent for the chemoselective hydrogenation of a range of ,-unsaturated carbonyl compounds [28,29], have been shown to be particularly useful for the hydrogenation of LA to produce GVL in an aqueous environment at temperatures as low as 50 °C.…”

Section: Introductionmentioning

confidence: 99%

Catalytic conversion of biomass-derived levulinic acid into γ-valerolactone using iridium nanoparticles supported on carbon nanotubes

Liu

Wang

et al. 2013

Chinese Journal of Catalysis

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A new method has been developed for the catalytic conversion of biomass-derived levulinic acid (LA) into -valerolactone (GVL) with molecular hydrogen (H2) using a series of heterogeneous noble metal catalysts. Excellent yields of the GVL were obtained under mild reaction conditions of 50°C and 2 MPa of H2 using iridium nanoparticles supported on carbon nanotubes (Ir/CNT). It is noteworthy that the reaction proceeded smoothly in the presence of formic acid (FA, co-produced with LA in equimolar amounts during the acid-mediated hydrolysis of lignocellulosic biomass). Furthermore, the FA remained intact, highlighting the practical advantages of this process for the convenient and cost-effective processing of a biomass-derived LA/FA solution. The method is effective for the simultaneous production of GVL and FA from a wide variety of renewable biomass resources.

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Section: Introductionmentioning

confidence: 99%

Catalytic conversion of biomass-derived levulinic acid into γ-valerolactone using iridium nanoparticles supported on carbon nanotubes

Liu

Wang

et al. 2013

Chinese Journal of Catalysis

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“…The group-9 and group-10 metals, such as Rh, Ir, Ni, Pd, and Pt, are well known to generally hydrogenate the C=C bond more easily than the C=O bond of α,β-unsaturated aldehydes [2]. Despite extensive research [3][4][5], only Ir-, Os-, and Pt-based catalysts have thus far produced unsaturated alcohols [6][7][8]. To improve the chemoselective hydrogenation of the C=O group, the modification of the previously mentioned metals is necessary, i.e., the addition of more electropositive metals [9] or the use of oxide supports that strongly interact with the active metals [10].…”

Section: Introductionmentioning

confidence: 99%

Development of Nanoporous Ni-Sn Alloy and Application for Chemoselective Hydrogenation of Furfural to Furfuryl Alcohol

Rodiansono

Hara

Ichikuni

et al. 2013

Bull. Chem. React. Eng. Catal.

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A very simple synthetic procedure was developed for the preparation of Ni-Sn alloy catalysts that were utilised for chemoselective hydrogenation of furfural, producing furfuryl alcohol almost exclusively. The mixture of nickel nanoparticles supported on aluminum hydroxide (R-Ni/AlOH) and a solution containing tin was treated under hydrothermal condition, producing the as prepared nickel-tin alloy supported on aluminum hydroxide (Ni-Sn/AlOH). H2 treatment at range of temperature of 673-873 K for 1.5 h to the as prepared Ni-Sn/AlOH produced nanoporous Ni-Sn alloy catalysts. XRD patterns and SEM images revealed that the formation of Ni-Sn alloy of Ni3Sn and Ni3Sn2 phases and the transformation of crystalline gibbsite and bayerite into amorphous alumina were clearly observed after H2 treatment at 873 K. The formation of the Ni-Sn alloy may have played a key role in the enhancement of the chemoselectivity.

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“… Transformations of testosterone ((a) and (b)) and epiandrosterone ((c) and (d)) steroids involving the activation of carbonyl groups. Stoichiometric, or catalytic conditions employed.…”

Section: Methodsmentioning

confidence: 99%

Boosting the Catalytic Performance of Metal–Organic Frameworks for Steroid Transformations by Confinement within a Mesoporous Scaffold

et al. 2017

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Solid-state crystallization achieves selective confinement of metal-organic framework (MOF) nanocrystals within mesoporous materials,t herebyr endering active sites more accessible compared to the bulk-MOF and enhancing the chemical and mechanical stability of MOF nanocrystals. (Zr)UiO-66(NH 2 )/SiO 2 hybrid materials were tested as efficient and reusable heterogeneous catalysts for the synthesis of steroid derivatives,o utperforming the bulk (Zr)UiO-66(NH 2 ) MOF.Aclear correlation between the catalytic activity of the dispersed Zr sites present in the confined MOF,and the loading of the mesoporous SiO 2 ,i sd emonstrated for steroid transformations.Scheme 1. Transformations of testosterone((a) and (b)) and epiandrosterone((c) and (d)) steroids involving the activation of carbonyl groups. Stoichiometric [9a,k] or catalytic conditions [8b, 9g] employed.

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Chemoselective Reduction of Complex α,β‐Unsaturated Ketones to Allylic Alcohols over Ir‐Metal Particles on β Zeolites

Cited by 63 publications

References 13 publications

Catalytic conversion of biomass-derived levulinic acid into γ-valerolactone using iridium nanoparticles supported on carbon nanotubes

Catalytic conversion of biomass-derived levulinic acid into γ-valerolactone using iridium nanoparticles supported on carbon nanotubes

Development of Nanoporous Ni-Sn Alloy and Application for Chemoselective Hydrogenation of Furfural to Furfuryl Alcohol

Boosting the Catalytic Performance of Metal–Organic Frameworks for Steroid Transformations by Confinement within a Mesoporous Scaffold

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