Transition‐Metal‐Catalysed Transfer Hydrogenation Reactions with Glycerol and Carbohydrates as Hydrogen Donors

Ansari, Mohd Farhan; Anshika,; Sortais, Jean‐Baptiste; Elangovan, Saravanakumar

doi:10.1002/ejoc.202301278

Cited by 3 publications

(1 citation statement)

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“…Finally, to the best of our knowledge, there are no publications studying the transfer hydrogenation of furfural with glycerol as a hydrogen donor, despite publications indicating its transfer hydrogenation capacity and the generation of dihydroxyacetone (DHA) and/or lactic acid coproducts. − Hence, due to its potential low cost as a byproduct from biodiesel production, further research should also consider glycerol as a hydrogen donor, with focus on coproducing DHA, a high-value (US$25,000/tonne) compound mainly used for self-tanning products . As discussed previously, a significant advantage of CTH is the possibility of selling the dehydrogenated hydrogen donor coproduct, generating additional revenue.…”

Section: Results and Discussionmentioning

confidence: 99%

Conceptual Process Design, Techno-Economics, and Greenhouse Gas Analysis of Furfuryl Alcohol Production via Transfer Hydrogenation

Fraga,

Ramirez,

Renouf

et al. 2024

ACS Sustainable Chem. Eng.

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Catalytic transfer hydrogenation (CTH) has gained attention as a potentially more sustainable process than conventional hydrogenation with H2 gas. In this process, hydrogen is supplied in situ from a donor molecule without the need for high-pressure H2. We developed a conceptual commercial process for the transfer hydrogenation of furfural into furfuryl alcohol (FFA) and performed techno-economic and greenhouse gas (GHG) analyses aiming to identify bottlenecks and guide future research in this field. Two hydrogen donor compounds were considered: 2-propanol and ethanol. Total capital investment varies between US$24.9 and 33.4 million for these processes, and the minimum selling price for FFA is below the market price of US$1.52/kg only with ethanol as a hydrogen donor. The main impact on the profitability is from selling the dehydrogenated hydrogen donor as a coproduct. Thus, low-cost hydrogen donors that generate high-value dehydrogenation products are required for this process to be competitive with conventional hydrogenation. In addition, utilizing a hydrogen donor that comes free of embodied impact and/or that avoids a GHG release is required for CTH to have a lower GHG emission intensity than conventional hydrogenation.

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Section: Results and Discussionmentioning

confidence: 99%

Conceptual Process Design, Techno-Economics, and Greenhouse Gas Analysis of Furfuryl Alcohol Production via Transfer Hydrogenation

Fraga,

Ramirez,

Renouf

et al. 2024

ACS Sustainable Chem. Eng.

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Ruthenium‐Catalyzed Chemoselective Olefin Transfer Hydrogenation of alpha, beta‐Unsaturated Carbonyl Systems By Using EtOH as Hydrogen Source

Beaufils,

Albrecht

2024

ChemCatChem

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The use of EtOH as hydrogen donor is remarkably underexplored in transfer hydrogenation reactions, even though EtOH represents an appealing hydrogen source. With the cationic ruthenium complex [Ru(PYA)(cymene)]+, 1, containing a N,N‐bidentate amino‐functionalized pyridinium amidate (PYA) ligand as catalyst precursor, we here demonstrate the first example of chemoselective transfer hydrogenation of the C=C bond in α,β‐unsaturated ketones using EtOH as benign hydrogen source to yield a variety of functionalized ketones. The reaction proceeds under mild conditions with K2CO3 as base and conventiantly at room temperature. A broad substrate scope, including various functionalized α,β‐unsaturated carbonyl groups, demonstrates the general applicability of this method. Preliminary mechanistic studies suggest the formation of an alkoxide complex [1]–OEt as an initially formed species, and the requirement for EtOH to induce hydride transfer, suggesting a protic activation of the catalyst.

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Hybrid Metal Catalysts as Valuable Tools in Organic Synthesis: An Overview of the Recent Advances in Asymmetric C─C Bond Formation Reactions

Rimoldi,

Coffetti,

Gandolfi

et al. 2024

Molecules

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Carbon–carbon bond formation represents a key reaction in organic synthesis, resulting in paramount importance for constructing the carbon backbone of organic molecules. However, traditional metal-based catalysis, despite its advantages, often struggles with issues related to efficiency, selectivity, and sustainability. On the other hand, while biocatalysis offers superior selectivity due to an extraordinary recognition process of the substrate, the scope of its applicable reactions remains somewhat limited. In this context, Artificial Metalloenzymes (ArMs) and Metallo Peptides (MPs) offer a promising and not fully explored solution, merging the two fields of transition metal catalysis and biotransformations, by inserting a catalytically active metal cofactor into a customizable protein scaffold or coordinating the metal ion directly to a short and tunable amino acid (Aa) sequence, respectively. As a result, these hybrid catalysts have gained attention as valuable tools for challenging catalytic transformations, providing systems with new-to-nature properties in organic synthesis. This review offers an overview of recent advances in the development of ArMs and MPs, focusing on their application in the asymmetric carbon–carbon bond-forming reactions, such as carbene insertion, Michael additions, Friedel–Crafts and cross-coupling reactions, and cyclopropanation, underscoring the versatility of these systems in synthesizing biologically relevant compounds.

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Transition‐Metal‐Catalysed Transfer Hydrogenation Reactions with Glycerol and Carbohydrates as Hydrogen Donors

Cited by 3 publications

References 103 publications

Conceptual Process Design, Techno-Economics, and Greenhouse Gas Analysis of Furfuryl Alcohol Production via Transfer Hydrogenation

Conceptual Process Design, Techno-Economics, and Greenhouse Gas Analysis of Furfuryl Alcohol Production via Transfer Hydrogenation

Ruthenium‐Catalyzed Chemoselective Olefin Transfer Hydrogenation of alpha, beta‐Unsaturated Carbonyl Systems By Using EtOH as Hydrogen Source

Hybrid Metal Catalysts as Valuable Tools in Organic Synthesis: An Overview of the Recent Advances in Asymmetric C─C Bond Formation Reactions

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