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RESEARCH PAPER · Chemical Reviews · 2020

Guidelines to Achieving High Selectivity for the Hydrogenation of α,β-Unsaturated Aldehydes with Bimetallic and Dilute Alloy Catalysts: A Review

Mathilde Luneau, Jin Soo Lim, Dipna A. Patel, E. Charles H. Sykes, C. M. Friend, Philippe Sautet

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Guidelines to Achieving High Selectivity for the Hydrogenation of α,β-Unsaturated Aldehydes with Bimetallic and Dilute Alloy Catalysts: A ReviewOriginalAtom efficient PtCu bimetallic catalysts and ultra dilute alloys for the selective hydrogenation of furfural89Chemoselective hydrogenation of α,β-unsaturated carbonyl compounds using a recyclable Ru catalyst embedded on a bisphosphine based POP15Bimetallic RuNi nanoparticles as catalysts for upgrading biomass: metal dilution and solvent effects on selectivity shifts24Factors controlling oxophilicity and carbophilicity of transition metals and main group metals69Hydrogenation of pentenal over supported Pt nanoparticles: influence of Lewis-acid sites in the conversion pathway10Interfacial Hydroxyl Promotes the Reduction of 4-Nitrophenol by Ag-based Catalysts Confined in Dendritic Mesoporous Silica Nanospheres46Direct Heterogenization of the Ru-Macho Catalyst for the Chemoselective Hydrogenation of α,β-Unsaturated Carbonyl Compounds39Adsorption of crotonaldehyde on metal surfaces: Cu vs Pt17Reductive Conversion of Biomass-Derived Furancarboxylic Acids with Retention of Carboxylic Acid Moiety30Edge‐Confined Pt1/MoS2 Single‐Atom Catalyst Promoting the Selective Activation of Carbon‐Oxygen Bond35The Promotion Effect of Cu on the Pd/C Catalyst in the Chemoselective Hydrogenation of Unsaturated Carbonyl Compounds3Exploring paths of chemical transformations in molecular and periodic systems: An approach utilizing force136Nanoglobular carbon and palladium–nanoglobular carbon catalysts for liquid-phase hydrogenation of organic compounds26Boosting selective hydrogenation through hydrogen spillover on supported-metal catalysts at room temperature127Dilute Pd-in-Au alloy RCT-SiO2 catalysts for enhanced oxidative methanol coupling24Surface Molecule Manipulated Pt/TiO 2 Catalysts for Selective Hydrogenation of Cinnamaldehyde40Formation of a Ti–Cu(111) single atom alloy: Structure and CO binding19The roles of metal-promoter interface on liquid phase selective hydrogenation of crotonaldehyde over Ir-MoOx/BN catalysts13Hydrogenation of Cinnamaldehyde on Cu(110) Single-Crystal Surfaces13The Influence of Surface Structure of RhPt Bimetallic Nanoparticles on the Hydrogenation of Aromatic Compounds18Regeneration of Active Surface Alloys during Cyclic Oxidation and Reduction: Oxidation of H2 on Pd/Ag(111)9Selective Interactions between Free-Atom-like d-States in Single-Atom Alloy Catalysts and Near-Frontier Molecular Orbitals107Cinnamaldehyde adsorption and thermal decomposition on copper surfaces6PdCu single atom alloys supported on alumina for the selective hydrogenation of furfural122Creating High Regioselectivity by Electronic Metal–Support Interaction of a Single-Atomic-Site Catalyst149Spatial Location and Microenvironment Engineering of Pt-CeO2 Nanoreactors for Selective Hydrogenation of Cinnamaldehyde to Cinnamyl Alcohol24Ethanol on Graphite: Ordered Structures and Delicate Balance of Interfacial and Intermolecular Forces5Preparation of Reduced-Graphene-Oxide-Supported CoPt and Ag Nanoparticles for the Catalytic Reduction of 4-Nitrophenol15Supported ruthenium catalysts for the aqueous-phase selective hydrogenation of furfural to furfuryl alcohol33Adsorption of acrolein and its hydrogenation products on Cu(111)4Controllable Preparation of Hierarchical Mnco Bimetallic Photocatalyst and the Effect of Atomic Ratio on its Photocatalytic Activity17Controlled hydrogenation of a biomass-derived platform chemical formed by aldol-condensation of 5-hydroxymethyl furfural (HMF) and acetone over Ru, Pd, and Cu catalysts27Efficient electrocatalytic hydrogenation of cinnamaldehyde to value-added chemicals35Fe 2 O 3 supported Pt single atom catalysts for the selective hydrogenation of cinnamaldehyde8Improvement and regeneration of Co–B amorphous alloy nanowires for the selective hydrogenation of cinnamaldehyde10Microenvironment engineering of supported metal nanoparticles for chemoselective hydrogenation27Theoretical design of platinum–sliver single atom alloy catalysts with CO adsorbate-induced surface structures10Thermodynamics regulated organic hydride/acid pairs as novel organic hydrogen reductants9Ultra-Dilute High-Entropy Alloy Catalyst with Core-Shell Structure for High-Active Hydrogenation of Furfural to Furfuryl Alcohol at Mild Temperature63Carbon encapsulated bimetallic FeCo nanoalloys for one-step hydroxylation of benzene to phenol27Synthesis of aluminum doped MIL-100(Fe) compounds for the one-pot photocatalytic conversion of cinnamaldehyde and benzyl alcohol to the corresponding alcohol and aldehyde under anaerobic conditions28Selective Acrolein Hydrogenation over Ligand-Protected Gold Clusters: A Venus Flytrap Mechanism11Comment on “STM study of the (111) and (100) surfaces of PdAg, Surf. Sci. 417 (1998) 292–300″ and references therein2Molecular and Dissociative Hydrogen Adsorption on Bimetallic PdAg/Pd(111) Surface Alloys: A Combined Experimental and Theoretical Study12Decoding reactive structures in dilute alloy catalysts88Highly stable Pt–Co bimetallic catalysts prepared by atomic layer deposition for selective hydrogenation of cinnamaldehyde11Selective hydrogenation of furfural to furfuryl alcohol in water under mild conditions over a hydrotalcite-derived Pt-based catalyst133Size-Dependent Pt Nanoparticle/Carbon-Catalyzed Hydrogenation of 6-Chloroquinoline9Epsilon Cobalt Nanoparticles as Highly Performant Catalysts in Cinnamaldehyde Selective Hydrogenation13Geometrically embedding dispersive Pt nanoparticles within silicalite-1 framework for highly selective ɑ, β-unsaturated aldehydes hydrogenation via oriented C = O adsorption configuration36Engineering electrophilic atomic Ir sites on CeO2 colloidal spheres for selectivity control in hydrogenation of α,β-unsaturated carbonyl compounds17CuO–Ru0.3@Co3O4 nanocomposites act as a tandem catalyst for dehydrogenation of ammonia borane and hydrogenation of nitrobenezene8Surface modification of metallic catalysts for the design of selective processes17Lignin Residue-Derived Carbon-Supported Nanoscale Iron Catalyst for the Selective Hydrogenation of Nitroarenes and Aromatic Aldehydes19Haptophilicity and Substrate-Directed Reactivity in Diastereoselective Heterogeneous Hydrogenation13A Cost-Effective Way to Produce Gram-Scale 18O-Labeled Aromatic Aldehydes12Synthesis of Dual-Active-Sites Ni-Ni2In catalysts for selective hydrogenation of furfural to furfuryl alcohol41Noble Metal-Free 2D 1T-MoS2 Edge Sites Boosting Selective Hydrogenation of Maleic Anhydride58Dynamical Study of Adsorbate-Induced Restructuring Kinetics in Bimetallic Catalysts Using the PdAu(111) Model System51Hydrogenation and hydrogenolysis of 5-hydroxymethylfurfural to 2,5-dimethylfuran via synergistic catalysis of Ni2In and acid-base sites35Active learning of reactive Bayesian force fields applied to heterogeneous catalysis dynamics of H/Pt147Facilitating Hydrogen Dissociation over Dilute Nanoporous Ti–Cu Catalysts31Adsorption, thermal conversion, and catalytic hydrogenation of acrolein on Cu surfaces11Pt‐WOx/C Catalysts for α, β‐Unsaturated Aldehydes Hydrogenation: An NMR Study of the Effect of the Reactant Adsorption on Activity and Selectivity10Highly selective electrocatalytic hydrogenation of cinnamaldehyde over tin dioxide-supported palladium nanocatalysts14Modifying Interface of Carbon Support-Stimulated Hydrogen Spillover for Selective Hydrogenation16Synergy of metal nanoparticles and organometallic complex in NAD(P)H regeneration via relay hydrogenation31PtMx/SBA-15 (M = Co, Cu, Ni and Zn) bimetallic catalysts for crotonaldehyde selective hydrogenation9Promoting electrocatalytic hydrogenation of 5-hydroxymethylfurfural using buffer electrolytes as proton-donating motifs: Theoretical predictions and experimental validations42Creation of Well-Defined Pd Surface Sites on Single Crystal Pd33Ag67: From Ensembles to Single Atoms2In situ identification of surface sites in Cu–Pt bimetallic catalysts: Gas-induced metal segregation10In-situ reconstruction of single-atom Pt on Co3O4 for hydrogenation22Geometric and Electronic Effects in Hydrogenation Reactions62Catalytic Hydrogenation Reactions of Lignocellulosic Biomass-derived Compounds as a Strategy to Obtain Value-added Products2Thermocatalytic and photocatalytic chemoselective reduction of cinnamaldehyde to cinnamyl alcohol and hydrocinnamaldehyde over Ru@ZnO/CN29Citral Hydrogenation over Dilute Alloy Catalysts7Rational design of bimetallic nanoparticles based catalysts : application for apgrading biomass0Enhanced Activity of Alkali-Treated ZSM-5 Zeolite-Supported Pt-Co Catalyst for Selective Hydrogenation of Cinnamaldehyde10Efficient Ni Ir alloy catalyst for selective hydrogenation of benzonitrile, crotonaldehyde and benzylideneacetone5Aqueous-Phase Hydrogenation of Furfural in the Presence of Supported Metal Catalysts of Different Types. A Review12AQUEOUS-PHASE HYDROGENATION OF FURFURAL IN THE PRESENCE OF SUPPORTED METALLIC CATALYSTS OF DIFFERENT TYPES. A REVIEW1Crotonaldehyde Adsorption on Cu-Pt Surface Alloys: A Quantum Mechanics Study9Production of 2-methyl furan, a promising 2nd generation biofuel, by the vapor phase hydrodeoxygenation of biomass-derived furfural over TiO2 supported Cu Ni bimetallic catalysts21Low-temperature dehydrogenation of dodecahydro-N-ethylcarbazole catalyzed by PdCo bimetallic oxide23Self-adaptively electronic transfer of ternary Ni3Ga0.8In0.2/SiO2 alloy catalysts toward enhancing selectivity hydrogenation4Synthesis of highly efficient Nano- Ni-Pt catalyst in a rotating packed bed for cinnamaldehyde hydrogenation13Bimetallic Sites for Catalysis: From Binuclear Metal Sites to Bimetallic Nanoclusters and Nanoparticles689Copper Growth on a Stepped Nickel Surface: Electronic and Geometric Effects on CO Reactivity11Highly Efficient Selective Hydrogenation of Cinnamaldehyde to Cinnamyl Alcohol over CoRe/TiO2 Catalyst7Quantum Mechanical Prediction and Experimental Verification of Au(I)-Catalyzed Substitution-Controlled Syntheses of 1H-Pyrido[4,3-b]indole and Spiro[indoline-3,3′-pyridine] Derivatives11Peripheral Coordination-Dependent Descriptor for Selective Interactions between Near-Frontier Molecular Orbitals and Single-Atom Catalysts11The Hydrogenation of Crotonaldehyde on PdCu Single Atom Alloy Catalysts15Metal oxides confine single atoms toward efficient thermal catalysis40Pd/oCNT Monolithic Catalysts for Continuous-Flow Selective Hydrogenation of Cinnamaldehyde14Nanoengineered Design of inside‐Heating Hot Nanoreactor Surrounded by Cool Environment for Selective Hydrogenations291T‐phase MoS 2 edge‐anchored Pt 1 −S 3 active site boosting selective hydrogenation of biomass‐derived maleic anhydride9Three-Component Chemo-Selective Synthesis of N-(o-Alkenylaryl) Pyrazoles by Pyrazole Annulation and Rh-Catalyzed Chemo-Selective Aryl C–H Addition Cascade26A facile strategy for incorporation of PtCo alloy into UiO-66-NH2 for cinnamaldehyde hydrogenation13“Cocktail”-type catalysis on bimetallic systems for cinnamaldehyde selective hydrogenation: Role of isolated single atoms, nanoparticles and single atom alloys16Recent Advances on Heterogeneous Non-noble Metal Catalysts toward Selective Hydrogenation Reactions164PtCo/MWCNTs Prepared by a Microwave‐assisted Polyol Method for Selective Cinnamaldehyde Hydrogenation6Enriching Pt3 ensemble with isolated 3-fold hollow site by crystal-phase engineering of Pt3Fe single-nanoparticle for acetylene hydrogenation12Electro-oxidation cross-coupling of primary and secondary alcohols by constructing intermediate-enriched micro-environment15Dioxygen‐Triggered β‐Hydroxysulfonylation of Terminal Olefins Controlled by DABCO4Selective coordination activation regulating the selectivity for photocatalytic hydrogenation of α, β-unsaturated aldehyde over Pd/MIL-100(FeaCub)22High Selectivity and Activity of Ti-Cu(111) Dilute Alloys for the Deoxygenation of Ethanol to Ethylene10Thermodynamic Evaluations of Amines as Hydrides or Two Hydrogen Ions Reductants and Imines as Protons or Two Hydrogen Ions Acceptors, as Well as Their Application in Hydrogenation Reactions5Electron synergy effect in the PtCo/CNTs bimetallic catalysts for promoting highly selective and stable hydrogenation of crotonaldehyde6Identifying the Optimal Pd Ensemble Size in Dilute PdAu Alloy Nanomaterials for Benzaldehyde Hydrogenation17Rational design of catalysts for heterogeneous selective hydrogenation of unsaturated aldehydes/ketones: From nanoparticles to single atoms16Highly selective transfer hydrogenation of α,β-unsaturated aldehydes by frustrated Lewis pairs (FLPs) on oxygen-defect-rich Co3O4@NC16Selective electrocatalytic hydrogenation of lignocellulose-derived 5-hydroxymethylfurfural with superior productivities10Geometric and Electronic Effects in the Binding Affinity of Imidazole-Based N-Heterocyclic Carbenes to Cu(100)- and Ag(100)-Based Pd and Pt Single-Atom Alloy Surfaces3Thiophene Modification of the Pt/SOD Catalyst to Enhance Catalytic Selectivity in Hydrogenation Reactions5Acrolein Hydrogenation Catalyzed by Pt(111): Effect of Carbonaceous Deposits on Kinetics5Bimetallic FexPt100–x Nanoparticles Immobilized on Supported Ionic Liquid Phases as Hydrogenation and Hydrodeoxygenation Catalysts: Influence of the Metal Content on Activity and Selectivity9Carbon-supported Pd/NiO-CoOx nanoparticles for highly selective and stable 1-nitroanthraquinone hydrogenation1Designing Efficient Single-Atom Alloy Catalysts for Selective C═O Hydrogenation: A First-Principles, Active Learning and Microkinetic Study21Carbon-Coated Ni-Fe Nanocatalysts: Bridging the Gap in Cinnamaldehyde Hydrogenation Performance and Durability5Ruthenium-Picolylamine-Incorporated Mixed-Linker MOFs: Highly Active Heterogeneous Catalysts for Olefin and Aldehyde Hydrogenation9Aqueous phase selective CO hydrogenation of cinnamaldehyde over bimetallic RuCo catalysts with electronic and geometric modification15Selective Hydrogenation of Cinnamaldehyde, Furanic, and Aromatic Aldehydes over a Z-Scheme Heterojunction Photocatalyst Constituted of Pd NPs Supported on g-C3N4/ZnO Nanocomposite21Photoinduced catalytical reduction of carbonyl compounds using water as a hydrogen source5Selective hydrogenolysis of 5-hydroxymethylfurfural to 2,5-dimethylfuran with high yield over bimetallic Ru–Co/AC catalysts18The nature of crystal facet effect of TiO 2 -supported Pd/Pt catalysts on selective hydrogenation of cinnamaldehyde: electron transfer process promoted by interfacial oxygen species6Thermodynamic evaluations of the acceptorless dehydrogenation and hydrogenation of pre-aromatic and aromatic N-heterocycles in acetonitrile1Theoretical Insights into H 2 Activation over Anatase TiO 2 Supported Metal Adatoms34Porous Composite‐Mediated Bimetallic Cluster POMs/Zr‐MOF for Catalytic Transfer Hydrogenation of Biomass‐Derived Aldehydes and Ketones39Synthesis of Kaolin-Supported Nickel Oxide Composites for the Catalytic Oxidative Degradation of Methylene Blue Dye27Tuning the Hydrogenation Selectivity of an Unsaturated Aldehyde via Single-Atom Alloy Catalysts50Mechanistic insights on the promoting roles of IrFe alloy in selective hydrogenation of crotonaldehyde9Spatially isolated dual-active sites enabling selective hydrogenation20Selective Hydrogenation of Alkyne by Atomically Precise Pd6 Nanocluster Catalysts: Accurate Construction of the Coplanar and Specific Active Sites30Boosting selective hydrogenation of α,β-unsaturated aldehydes through constructing independent Pt and Fe active sites on support25Diastereoselective Hydrogenation of Tetrasubstituted Olefins using a Heterogeneous Pt‐Ni Alloy Catalyst2Diastereoselective Hydrogenation of Tetrasubstituted Olefins using a Heterogeneous Pt‐Ni Alloy Catalyst13An interesting synergistic effect of heteronuclear dual-atom catalysts for hydrogen production: Offsetting or promoting9Interfacial Chemistry and Catalysis of Inorganic Materials1Highly Selective Hydrogenation of Unsaturated Aldehydes in Aqueous Phase14Pt/Fe-TiO2-Catalyzed Selective Carbonyl Hydrogenation: Fe-Promoted Hydrogen Spillover62Ni–Al2O3/CN Nanocatalysts for Selective Hydrogenation of Furfural11Structural and chemical transformations of CuZn alloy nanoparticles under reactive redox atmospheres: An in situ TEM study29Hydrogenation of olefinic bonds in nitrile butadiene rubber on single-atom Pd1/CeO2−x catalysts with ultrahigh mass activity and stability15Adsorption of Acrolein, Crotonaldehyde, and Cinnamaldehyde on Pt(111) Surfaces: A Comparative DFT Study6Controlling hydrogenation of C=C and C=O bonds in cinnamaldehyde using Pt 1 /Ni and Pt 1 /Co single‐atom alloy catalysts16Targeted electron transfer effect of enzyme-like Co-NX catalysts for enhanced C = O hydrogenation16Precise regulation of Mo2N–TiO2 deposited Pt nanoparticles induced synergistic effect for the hydrogenation of cinnamaldehyde9Selective furfural hydrodeoxygenation over Cu-Fe catalysts with In-Situ Cu@Fe3O4 formation7Cis-trans adsorption configuration influenced high-efficient hydrogenation of furfural over zeolite-encapsulated PtCu bimetallic catalyst13Pt–Fe–Al Trimetallic Nanoporous Catalyst for Selective Hydrogenation of α,β-Unsaturated Aldehydes9

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