Sondre Hilmar Hopen Eliasson

• Foscato, Marco; Occhipinti, Giovanni; Eliasson, Sondre Hilmar Hopen & Jensen, Vidar Remi (2024). Automated de Novo Design of Olefin Metathesis Catalysts: Computational and Experimental Analysis of a Simple Thermodynamic Design Criterion. Journal of Chemical Information and Modeling. ISSN 1549-9596. 64(2), p. 412–424. doi: 10.1021/acs.jcim.3c01649. Full text in Research Archive Show summary

  Methods for computational de novo design of inorganic molecules have paved the way for automated design of homogeneous catalysts. Such studies have so far relied on correlation-based prediction models as fitness functions (figures of merit), but the soundness of these approaches has yet to be tested by experimental verification of de novo-designed catalysts. Here, a previously developed criterion for the optimization of dative ligands L in ruthenium-based olefin metathesis catalysts RuCl2(L)(L′)(═CHAr), where Ar is an aryl group and L′ is a phosphine ligand dissociating to activate the catalyst, was used in de novo design experiments. These experiments predicted catalysts bearing an N-heterocyclic carbene (L = 9) substituted by two N-bound mesityls and two tert-butyl groups at the imidazolidin-2-ylidene backbone to be promising. Whereas the phosphine-stabilized precursor assumed by the prediction model could not be made, a pyridine-stabilized ruthenium alkylidene complex (17) bearing carbene 9 was less active than a known leading pyridine-stabilized Grubbs-type catalyst (18, L = H2IMes). A density functional theory-based analysis showed that the unsubstituted metallacyclobutane (MCB) intermediate generated in the presence of ethylene is the likely resting state of both 17 and 18. Whereas the design criterion via its correlation between the stability of the MCB and the rate-determining barrier indeed seeks to stabilize the MCB, it relies on RuCl2(L)(L′)(═CH2) adducts as resting states. The change in resting state explains the discrepancy between the prediction and the actual performance of catalyst 17. To avoid such discrepancies and better address the multifaceted challenges of predicting catalytic performance, future de novo catalyst design studies should explore and test design criteria incorporating information from more than a single relative energy or intermediate.

• Giovanetti, Marinella de; Eliasson, Sondre Hilmar Hopen; Bore, Sigbjørn Løland; Eisenstein, Odile & Cascella, Michele (2024). Morphology of lithium halides in tetrahydrofuran from molecular dynamics with machine learning potentials. Chemical Science. ISSN 2041-6520. doi: 10.1039/d4sc04957h. Full text in Research Archive Show summary

  The preferred structures of lithium halides (LiX, with X = Cl, Br, I) in organic solvents have been the subject of a wide scientific debate, and a large variety of forms has been isolated and characterized by X-ray diffraction. The identified molecular scaffolds for LiX are diverse, often built on (LiX)n rings with a prevalence of rhomboidal arrangements and an appropriate number of solvent or Lewis base molecules coordinating the lithium ions. Much less is known about the structures of LiX in solution, limiting the understanding of the synergistic role of LiX in reactions with various organometallic complexes, as prominently represented by the turbo Grignard reaction. Here, we trained a machine learning potential on ab initio data to explore the complex conformational landscape for systems comprising four LiX moieties in tetrahydrofuran (THF). For all the considered halogens a large number of scaffolds were found at thermally accessible free energy values, indicating that LiX in solution are a diverse ensemble constituted of (LiX)n moieties of various sizes, completed by the appropriate number of coordinating THF. LiCl shows a preference for compact, pseudo-cubane Li4Cl4(THF)4 structures, coexisting with open rings. At concentrations close to the solubility limit, LiCl forms hexagonal structures, in analogy with literature observations on pre-nucleating NaCl. LiBr tends to favour less compact, more solvated aggregates. LiI significantly differs from the two other cases, producing highly solvated, monomeric, dimeric, or linear structures. This study provides a comprehensive view of LiX in organic solvent, revealing dynamical polymorphism that is not easily observable experimentally.

• Giovanetti, Marinella de; Eliasson, Sondre Hilmar Hopen; Bore, Sigbjørn Løland; Eisenstein, Odile & Cascella, Michele (2024). Morphology of Lithium Halides in Tetrahydrofuran from Molecular Dynamics with Machine Learning Potentials. ChemRxiv. ISSN 2573-2293. doi: 10.26434/chemrxiv-2024-mxjqn. Full text in Research Archive
• Giovanetti, Marinella de; Eliasson, Sondre Hilmar Hopen; Castro, Abril C; Eisenstein, Odile & Cascella, Michele (2023). Morphological Plasticity of LiCl Clusters Interacting with Grignard Reagent in Tetrahydrofuran. Journal of the American Chemical Society. ISSN 0002-7863. 145(30), p. 16305–16309. doi: 10.1021/jacs.3c04238. Full text in Research Archive Show summary

  Ab initio molecular dynamics simulations are used to explore tetrahydrofuran (THF) solutions containing pure LiCl and LiCl with CH3MgCl, as model constituents of the turbo Grignard reagent. LiCl aggregates as Li4Cl4, which preferentially assumes compact cubane-like conformations. In particular, an open-edge pseudotetrahedral frame is promoted by solvent-assisted Li–Cl bond cleavage. Among the Grignard species involved in the Schlenk equilibrium, LiCl prefers to coordinate MgCl2 through μ2-Cl bridges. Using a 1:1 Li:Mg ratio, the plastic tetranuclear LiCl cluster decomposes to a highly solvated mixed LiCl·MgCl2 aggregate with prevalent Li–(μ2-Cl)2–Mg rings and linear LiCl entities. The MgCl2-assisted disaggregation of Li4Cl4 occurs through transient structures analogous to those detected for pure LiCl in THF, also corresponding to moieties observed in the solid state. This study identifies a synergistic role of LiCl for the determination of the compounds present in turbo Grignard solutions. LiCl shifts the Schlenk equilibrium promoting a higher concentration of dialkylmagnesium, while decomposing into smaller, more soluble, mixed Li:Mg:Cl clusters.

• Eliasson, Sondre H. Hopen & Jensen, Vidar Remi (2019). Benefit of a hemilabile ligand in deoxygenation of fatty acids to 1-alkenes. Faraday discussions. ISSN 1359-6640. 220, p. 231–248. doi: 10.1039/c9fd00037b. Full text in Research Archive Show summary

  One of the most important tasks for chemistry in our time is to contribute to sustainable chemical production. A green industrial process for linear α-olefins, the arguably most important class of petrochemical intermediates, from renewable resources would be a major contribution to this end. Plant oils are attractive renewable feedstocks for this purpose because their triglycerides can be hydrolyzed to fatty acids that contain valuable long-chain hydrocarbons (C16–C22). These hydrocarbons may, in turn, be converted to α-olefins by the deoxygenation of the fatty acids. For the most selective of these deoxygenation reactions, transition-metal catalyzed decarbonylative dehydration, the density functional theory (DFT) calculations have just started to offer valuable mechanistic insight, and the use of this insight in rational catalyst design has been facilitated by the arrival of the first well-defined precatalyst for this reaction, Pd(cinnamyl)Cl(DPEphos) (1). Here, we present DFT calculations showing how, in 1, the hemilability of DPEphos, a classical P–O–P diphosphine, contributes to a low overall barrier and high α-selectivity. DPEphos facilitates decarbonylation by first switching from bidentate to monodentate binding to create a coordination site for CO. The recoordination of the dangling phosphine displaces the Pd-bound CO, a co-product that must leave the reactor for the reaction to proceed, and the escaping CO is here modelled using a low pressure in the calculation of its thermochemical corrections. Finally, the role of the hemilabile ligand suggests that further improvements in the decarbonylative dehydration of fatty acids to α-olefins might be achieved by exploring new, potentially asymmetric, hemilabile ligands.

• Eliasson, Sondre H. Hopen; Chatterjee, Anamitra; Occhipinti, Giovanni & Jensen, Vidar Remi (2019). Green Solvent for the Synthesis of Linear α-Olefins from Fatty Acids. ACS Sustainable Chemistry and Engineering. 7(5), p. 4903–4911. doi: 10.1021/acssuschemeng.8b05523. Full text in Research Archive
• Chatterjee, Anamitra; Eliasson, Sondre H. Hopen & Jensen, Vidar Remi (2018). Selective production of linear α-olefins via catalytic deoxygenation of fatty acids and derivatives. Catalysis Science & Technology. ISSN 2044-4753. 8(6), p. 1487–1499. doi: 10.1039/c7cy02580g. Full text in Research Archive Show summary

  Scientists are exploring renewables as sources for a more sustainable production of chemicals. Linear α-olefins (LAOs) are key commodity chemicals and petrochemical intermediates, which are currently almost exclusively obtained from fossil resources. The most important renewable alternative is plant oil, from which fatty acids and their derivatives can be converted into LAOs by ethenolysis of monounsaturated fatty acids or deoxygenation of saturated ones. The variety, in terms of length, is greater for the saturated fatty acids found in plant oils, and this review covers deoxygenation processes mediated by homogeneous, heterogeneous and enzymatic catalysts and discusses the strengths and weaknesses of different approaches for the selective production of LAOs. Although progress has been made in recent years, the best catalysts in each category are still far from fulfilling the industrial requirements for efficiency, atom economy, and turnover numbers. We hope that our focus on the main remaining challenges will stimulate future research to develop catalysed deoxygenation of fatty acid derivatives as a sustainable and industrially viable route to a range of α-olefins.

• Eliasson, Sondre H. Hopen; Chatterjee, Anamitra; Occhipinti, Giovanni & Jensen, Vidar Remi (2017). The Mechanism of Rh-Catalyzed Transformation of Fatty Acids to Linear Alpha olefins. Inorganics. 5(4). doi: 10.3390/inorganics5040087. Full text in Research Archive
• Chatterjee, Anamitra; Eliasson, Sondre H. Hopen; Törnroos, Karl Wilhelm & Jensen, Vidar Remi (2016). Palladium precatalysts for decarbonylative dehydration of fatty acids to linear alpha olefins. ACS Catalysis. 6(11), p. 7784–7789. doi: 10.1021/acscatal.6b02460. Full text in Research Archive
• Šoltészová, Veronika; Foscato, Marco; Eliasson, Sondre H. Hopen & Jensen, Vidar Remi (2015). Evolution inspector: Interactive visual analysis for evolutionary molecular design. In Chen, Min & Andrienko, Gennady (Ed.), Proceedings of the IEEE Conference on Visual Analytics Science and Technology. IEEE (Institute of Electrical and Electronics Engineers). ISSN 9781467397834. p. 219–220. doi: 10.1109/VAST.2015.7347687. Full text in Research Archive

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• Eliasson, Sondre Hilmar Hopen; Giovanetti, Marinella de; Bore, Sigbjørn Løland; Cascella, Michele & Eisenstein, Odile (2024). Machine Learned Potential for Organolithium Compounds in THF. Full text in Research Archive
• Eliasson, Sondre Hilmar Hopen; Giovanetti, Marinella de; Bore, Sigbjørn Løland; Cascella, Michele & Eisenstein, Odile (2024). Machine Learned Potential for Organolithium Compounds in THF. Full text in Research Archive
• Eliasson, Sondre Hilmar Hopen; Giovanetti, Marinella de; Bore, Sigbjørn Løland; Bortoli, Marco; Cascella, Michele & Eisenstein, Odile (2023). Machine Learned Potential for Organolithium in THF. Full text in Research Archive
• Eliasson, Sondre Hilmar Hopen; Giovanetti, Marinella de; Bore, Sigbjørn Løland; Bortoli, Marco & Cascella, Michele (2023). Machine Learned Potential for Organolithium Compounds in THF. Full text in Research Archive
• Foscato, Marco; Occhipinti, Giovanni; Eliasson, Sondre Hilmar Hopen & Jensen, Vidar Remi (2023). Automated De Novo Design and Experimental Validation of Ru-Catalysts for Metathesis: Testing the Limits of a Correlation-Based Design Criterion. Full text in Research Archive
• Tysse, Morten; Jensen, Vidar Remi; Børve, Knut J.; Eliasson, Sondre Hilmar Hopen & Uggerud, Einar (2021). Electrocatalytic Reduction of CO2 to CO by Iron and Zinc Porphyrin and Bacteriochlorin - A DFT study. Full text in Research Archive
• Eliasson, Sondre H. Hopen & Jensen, Vidar Remi (2019). The benefit of a hemilabile ligand in deoxygenation of fatty acids to 1-alkenes. Full text in Research Archive Show summary

  One of the most important tasks for chemistry in our time is to contribute to sustainable chemical production. A green industrial process for linear α-olefins, the arguably most important class of petrochemical intermediates, from renewable resources would be a major contribution to this end. Plant oils are attractive renewable feedstocks for this purpose because their fatty acids may be converted to α-olefins by deoxygenation.[1] For the most selective of these deoxygenation reactions, transition-metal catalyzed decarbonylative dehydration, the density functional theory (DFT) calculations have just started to offer valuable mechanistic insight,[2] and the use of this insight in rational catalyst design has been facilitated by the arrival of the first well-defined precatalyst for this reaction, Pd(cinnamyl)Cl(DPEphos) (A1).[3] Here, we present DFT calculations showing how, in A1, the hemilability of DPEphos, a classical P–O–P diphosphine, contributes to a low overall barrier and high α-selectivity. DPEphos facilitates decarbonylation by first switching from bidentate to monodentate binding to create a coordination site for CO. The recoordination of the dangling phosphine displaces the Pd-bound CO, a co-product that must leave the reactor for the reaction to proceed, and the escaping CO is here modelled using a low pressure in the calculation of its thermochemical corrections. Finally, the role of the hemilabile ligand suggests that further improvements in the decarbonylative dehydration of fatty acids to α-olefins might be achieved by exploring new, potentially asymmetric, hemilabile ligands.

• Heggstad, Katrine; Grønstad, Line Førre; Eliasson, Sondre H. Hopen; Ghaffari, Maryam; Lernevall, Lina Sophie Daughaard & Markova, Valeria [Show all 10 contributors for this article] (2017). Kunnskapskanalen: Forsker grandprix-2017 Bergen. [TV]. https://tv.nrk.no/serie/kunnskapskanalen/MDDP17002617/31-12-. Full text in Research Archive
• Chatterjee, Anamitra; Eliasson, Sondre H. Hopen & Jensen, Vidar Remi (2017). A heterogeneous catalyst for the sustainable synthesis of linear alpha olefins from renewable fatty acids. Full text in Research Archive
• Chatterjee, Anamitra; Eliasson, Sondre H. Hopen & Jensen, Vidar Remi (2017). Palladium catalysts for the transformation of fatty acids to alpha olefins. Full text in Research Archive
• Eliasson, Sondre H. Hopen; Chatterjee, Anamitra; Occhipinti, Giovanni & Jensen, Vidar Remi (2017). The Mechanism of Rh-Catalyzed Transformation of Fatty Acids to Alpha-olefins; A DFT-Study. Full text in Research Archive
• Eliasson, Sondre H. Hopen (2017). Omdanning av fornybart feitt til fossilt brennstoff vha. datasimuleringar. Full text in Research Archive
• Chatterjee, Anamitra; Eliasson, Sondre H. Hopen & Jensen, Vidar Remi (2017). Sustainable Transformation of Fatty Acids to Alpha-Olefins. Full text in Research Archive
• Foscato, Marco; Occhipinti, Giovanni; Eliasson, Sondre H. Hopen & Jensen, Vidar Remi (2017). In Silico Evaluation of Olefin Metathesis Catalysts: the Importance of Monitoring More than One Elementary Reaction. Full text in Research Archive
• Chatterjee, Anamitra; Eliasson, Sondre H. Hopen & Jensen, Vidar Remi (2016). New Organometallic Catalyst for Biomass Valorization. Full text in Research Archive Show summary

  Linear alpha-olefins count among the most important industrial intermediates and are used in the production of polymers and other materials and chemicals. Currently, these olefins are almost exclusively produced from fossil resources. As the world’s oil reserves continue to diminish and global warming looms, production of alpha olefins from renewable feedstocks is an important goal. One of the most promising routes in this respect is transition-metal-catalyzed decarbonylative dehydration of fatty acids. However, the decarbonylative dehydration reaction is still poorly understood and the existing catalysts and processes are not efficient enough for industrial implementation. Here we present new and more efficient organometallic catalysts for this reaction, catalysts that, under mild conditions, reach higher TOFs and require less phosphine excess than previously reported catalysts.

• Chatterjee, Anamitra; Eliasson, Sondre H. Hopen & Jensen, Vidar Remi (2016). Synthesis of Alpha-Olefins from Renewable Fatty Acids. Full text in Research Archive
• Chatterjee, Anamitra; Eliasson, Sondre H. Hopen & Jensen, Vidar Remi (2016). Palldium Precatalysts for Decarbonylative Dehydration of Fatty Acids to Linear Alpha Olefins. Full text in Research Archive
• Eliasson, Sondre H. Hopen; Foscato, Marco; Occhipinti, Giovanni & Jensen, Vidar Remi (2015). Automated Prediction of Optimized Ruthenium Catalysts for Olefin Metathesis. Full text in Research Archive
• Eliasson, Sondre H. Hopen; Foscato, Marco; Occhipinti, Giovanni & Jensen, Vidar Remi (2015). Automated Prediction of Optimized Ruthenium Catalysts for Olefin Metathesis. Full text in Research Archive

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