An easily recoverable and recyclable homogeneous polyester-based Pd catalytic system for the hydrogenation of α,β-unsaturated carbonyl compounds

The efficient chemo-, regio-and stereoselective formation of saturated carbon-carbon fragment is the critical challenge of organic synthesis; therefore, developing new methods for formation of these bonds is paramount. The rising interest for reductive aldol-type reactions is conditioned by its versatile applications, allowing the efficient formation of carbon-carbon bonds. The review aims to highlight the advantages and disadvantage of reductive aldol-type reactions to total synthesis of pharmaceutical substances in order to summarize knowledge and encourage further investigation of the field.

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“…Although it resulted in 57 % yield at best for 2.2; we therefore will not go over details of the approach. [44]…”

Section: Chemistry-a European Journalmentioning

confidence: 99%

Reductive Aldol‐type Reactions in the Synthesis of Pharmaceuticals

Runikhina

Eremin

Chusov

2021

Chemistry A European J

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“…The chemoselective hydrogenation of selected α,β-unsaturated carbonyl compounds was carried out in toluene in the presence of the homogeneous precatalyst trans-Pd(OAc) 2 (L 1 ) 2 at 303 K. In all cases the corresponding saturated carbonyl compound was observed in a range of chemoselectivity between 46 and 100%, as shown in Table 2 [27].…”

Section: Hydrogenation Of C-c Double and Triple Bondsmentioning

confidence: 99%

“…The possibility to produce carboxylic end-capped PLA chains functionalized with nitrogen containing moieties, called macroligands by Giachi et al [25], allowed the synthesis of well-defined macrocomplexes containing metal cations, such as Pd(II) . The latter Pd-based macrocomplexes were efficiently used to catalyze hydrogenation reactions conducted in the homogeneous phase followed by an easy separation step, as reported by Giachi et al [26] and Bartoli et al [27]. Isotactic endfunctionalized PLA with opposite tacticity can be combined to form a supramolecular structure named stereocomplex [28].…”

Section: Introductionmentioning

confidence: 99%

Palladium‐Based Catalysts‐Supported onto End‐Functionalized Poly(lactide) for C–C Double and Triple Bond Hydrogenation Reactions

Frediani¹,

Oberhauser²,

Rosi³

et al. 2017

New Advances in Hydrogenation Processes - Fundamentals and Applications

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Poly(lactide) (PLA), which is the polymer that will be discussed in this chapter, was functionalized with nitrogen containing aromatic groups by means ring opening polymerization (ROP) reactions. The obtained macroligands were successfully employed to coordinate Pd(II), which chemoselectively hydrogenated αβ-unsaturated carbonyl compounds to give the saturated counterparts as main product. The catalyst could be easily recycled upon a simple filtration process. End-functionalized isotactic PLA chains were used to generate stereocomplexes, featured by a higher thermal and hydrolytic resistance. The chemical nature of the nitrogen ligand introduced at the chain end of PLA was exploited to stabilize Pdnanoparticles (Pd-NP s) by interactions of the aromatic or nitrogen functionality with the NP s-surface. The polymer-anchored Pd-NP s were generated by a classical approach which comprised the coordination of Pd(II) by the functional group followed by reduction with hydrogen or by the metal vapor synthesis technique. The polymersupported Pd-NP s were successfully applied to catalyze the selective hydrogenation of alkynes to the corresponding alkene and cinnamylalcohol to the corresponding saturated aldehyde. In this book chapter the synthesis and structure-performance relationship of the new hydrogenation catalysts will be discussed.

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“…In the open literature, it is reported to be efficiently hydrogenated under continuous-flow conditions by using Ni/Raney or Pd/C [8]. On the other hand, Rh/γ-Al 2 O 3 prepared by deposition of rhodium nanoparticles from mesitylene-solvated rhodium atoms stabilized by trioctylamine [9] or Pd-pyridine poly(l-lactide) macrocomplex [10] were effectively used in batch reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

The Role of Support Hydrophobicity in the Selective Hydrogenation of Enones and Unsaturated Sulfones over Cu/SiO2 Catalysts

Cavuoto

Zaccheria²,

Marelli³

et al. 2020

Catalysts

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The substitution of complex hydrides and Ni- and noble metal-based catalysts in the synthesis of pharma and fragrance products is a relevant topic in the green chemistry scenario. Here, we report that non-toxic, non-noble metal-based Cu/SiO2 catalysts are effective and very selective in the hydrogenation of α,β-unsaturated ketones, esters and sulfones under very mild conditions. Vanillyl acetone can be obtained in quantitative yield in 1 h at 90 °C and 1 bar of H2. High dispersion of the metallic phase and support wettability play a significant role in determining catalytic performance.

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An easily recoverable and recyclable homogeneous polyester-based Pd catalytic system for the hydrogenation of α,β-unsaturated carbonyl compounds

Cited by 9 publications

References 24 publications

Reductive Aldol‐type Reactions in the Synthesis of Pharmaceuticals

Reductive Aldol‐type Reactions in the Synthesis of Pharmaceuticals

Palladium‐Based Catalysts‐Supported onto End‐Functionalized Poly(lactide) for C–C Double and Triple Bond Hydrogenation Reactions

The Role of Support Hydrophobicity in the Selective Hydrogenation of Enones and Unsaturated Sulfones over Cu/SiO2 Catalysts

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