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Federsel, Hans-JürgenORCID iD iconorcid.org/0000-0001-5781-1689
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Publications (10 of 10) Show all publications
Carreiro, E. P., Hermann, G. J., Federsel, H.-J. & Burke, A. J. (2024). Asymmetric Additions Empowered by OrganoCatalysts, Metal Catalysts, and Deep Natural Eutectic Solvents (NADES). Journal of Organic Chemistry, 89, 6631
Open this publication in new window or tab >>Asymmetric Additions Empowered by OrganoCatalysts, Metal Catalysts, and Deep Natural Eutectic Solvents (NADES)
2024 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 89, p. 6631-Article in journal (Refereed) Published
Abstract [en]

This article is a history of an industrial-academic partnership that started almost two decades ago and details the evolution of a relationship between a small academic research group and a spin-out company located in Portugal. Their activities have ranged from the development of new metal-based catalytic systems for asymmetric epoxidations, allylic alkylations, and arylations to the development of novel cinchona-based organocatalysts for asymmetric hydrosilylations and Michael additions. Current common interests are centered on the development of novel chiral Natural Deep Eutectic Solvent systems, which they are investigating in different types of reaction systems.

Place, publisher, year, edition, pages
American Chemical Society, 2024
Keywords
Addition reactions; Eutectics; Hydrosilylation; Industrial research; Academic research; Allylic alkylation; Asymmetric addition; Asymmetric epoxidation; Catalytic system; Metal catalyst; Organocatalysts; Portugal; Research groups; Spin-out companies; Organocatalyst
National Category
Organic Chemistry
Identifiers
urn:nbn:se:ri:diva-73246 (URN)10.1021/acs.joc.4c00334 (DOI)2-s2.0-85192251856 (Scopus ID)
Note

EPC acknowledges the Fundac\u0327a\u0303o para a Cie\u0302ncia e a Tecnologia (FCT) for funding through the strategic project to LAQV-REQUIMTE (FCT/MCTES; UIDB/50006/2020|UIDP/50006/2020). AJB acknowledges FCT for funding through the strategic project UIDB/00313/2020 to Coimbra Chemistry Centre\u2013Institute of Molecular Sciences (CQC-IMS).

Available from: 2024-05-27 Created: 2024-05-27 Last updated: 2024-05-27Bibliographically approved
Carreiro, E. P., Federsel, H.-J., Hermann, G. J. & Burke, A. J. (2024). Stereoselective Catalytic Synthesis of Bioactive Compounds in Natural Deep Eutectic Solvents (NADESs): A Survey across the Catalytic Spectrum. Catalysts, 14(3), Article ID 160.
Open this publication in new window or tab >>Stereoselective Catalytic Synthesis of Bioactive Compounds in Natural Deep Eutectic Solvents (NADESs): A Survey across the Catalytic Spectrum
2024 (English)In: Catalysts, E-ISSN 2073-4344, Vol. 14, no 3, article id 160Article in journal (Refereed) Published
Abstract [en]

Deep eutectic solvents (DESs) are a mixture of two or more components, and at a particular composition, they become liquids at room temperature. When the compounds that constitute the DESs are primary metabolites namely, amino acids, organic acids, sugars, or choline derivatives, the DESs are called natural deep eutectic solvents (NADESs). NADESs fully represent green chemistry principles. These solvents are highly welcome, as they are obtained from renewable resources, and gratifyingly are biodegradable and biocompatible. They are an alternative to room-temperature ionic liquids (RTILs). From the pharmaceutical industry’s point of view, they are highly desirable, but they unfortunately have been rarely used despite their enormous potential. In this review, we look at their impact on the asymmetric catalytic synthesis of key target molecules via metal-based catalysis, biocatalysis, and organocatalysis. In many cases, the NADESs that have been used are chiral and can even promote enantioselective reactions; this crucial and very exciting aspect is also discussed and analyzed. © 2024 by the authors.

Place, publisher, year, edition, pages
Multidisciplinary Digital Publishing Institute (MDPI), 2024
National Category
Chemical Sciences
Identifiers
urn:nbn:se:ri:diva-72833 (URN)10.3390/catal14030160 (DOI)2-s2.0-85188683010 (Scopus ID)
Note

EPC acknowledges the Fundação para a Ciência e a Tecnologia (FCT) for funding through the strategic project to LAQV-REQUIMTE (FCT/MCTES; UIDB/50006/2020|UIDP/50006/2020). AJB acknowledges FCT for funding through the strategic project UIDB/00313/2020|UIDP/00313/2020 to Coimbra Chemistry Centre—Institute of Molecular Sciences (CQC-IMS)

Available from: 2024-05-14 Created: 2024-05-14 Last updated: 2024-05-14Bibliographically approved
Fonseca, D., Amorim, A., Carreiro, E., Ramalho, J., Hermann, G., Federsel, H.-J., . . . Burke, A. (2023). Sustainable OrganoCatalyzed Enantioselective Catalytic Michael Additions in Betaine derived Deep Eutectic Solvents. SynOpen, 7(3), 374
Open this publication in new window or tab >>Sustainable OrganoCatalyzed Enantioselective Catalytic Michael Additions in Betaine derived Deep Eutectic Solvents
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2023 (English)In: SynOpen, ISSN 2509-9396, Vol. 7, no 3, p. 374-Article in journal (Refereed) Published
Abstract [en]

The catalyst cinchonidine-squaramide was immobilized within three different deep eutectic solvents (DES): (Betaine: D-Sorbitol: Water), (Betaine: D-Xylitol: Water) and (Betaine: D-Mannitol: Water) and evaluated in a well-known asymmetric Michael addition. These reactions provided excellent yields (up to 99%) and enantioselectivities (up to 98%) using only 1 mol% of catalyst. It was also possible to achieve 9 cycles in reactions with DES (Betaine: D-Sorbitol: Water), proving the high recyclability of this system. In the reactions realized with only 0.5 mol% of catalyst, it was possible to achieve 5 cycles and the products were obtained with high yields (up to 95%) and excellent enantioselectivities (up to 94%), using DES (Betaine: D-Sorbitol: Water)..

Place, publisher, year, edition, pages
Georg Thieme Verlag, 2023
Keywords
Betaine, Cinchonidine-squaramide, Deep Eutectic Solvent (DES), Immobilization, Organocatalysis
National Category
Organic Chemistry
Identifiers
urn:nbn:se:ri:diva-65705 (URN)10.1055/a-2117-9971 (DOI)2-s2.0-85165607183 (Scopus ID)
Note

This work received financial support from the Fundação para a Ciência e Tecnologia (FCT Portugal) through the project UIDB/50006/2020 | UIDP/50006/2020.

Available from: 2023-08-09 Created: 2023-08-09 Last updated: 2024-06-07Bibliographically approved
Federsel, H.-J. (2023). What enables and blocks synthetic chemistry methods in becoming industrially significant?. Cell Reports Physical Science, 4(7), Article ID 101493.
Open this publication in new window or tab >>What enables and blocks synthetic chemistry methods in becoming industrially significant?
2023 (English)In: Cell Reports Physical Science, E-ISSN 2666-3864, Vol. 4, no 7, article id 101493Article, review/survey (Refereed) Published
Abstract [en]

What factors will play a role in the decision process when looking at the reasons for certain reactions being adopted for large-scale industrial applications? An examination reveals that there are several parameters that have the power to be influential in this regard, either on their own or in combination, all dependent on the circumstances. Seen from a pharmaceutical manufacturing point of view, only certain structural motifs are of interest for in-depth investigations and, hence, are in demand of synthetic methodologies allowing the preparation of quantities beyond what sensibly is achieved by ordinary laboratory procedures. This inevitably leads to many reactions and even reaction types to fall by the wayside. A further criterion to fulfill is that a given synthesis must perform in a robust and consistent manner, irrespective of scale. Many methods used in the laboratory are demanding but can be handled and controlled by scientists well-versed in the art of organic synthesis. On scale-up, such reactions could behave in a capricious way, for example under the influence of issues with heat transfer and stirring efficiency, sensitivity to trace amounts of water, or being exposed to a non-inert atmosphere, which could lead to various levels of problems or even complete failure. Another significant aspect is that a key performance indicator in medicinal chemistry is the capability to make novel chemical compounds amenable to patent protection. This “race” into the unknown will inevitably demand the discovery and development of unprecedented synthetic methodologies, which eventually will have to prove their capabilities on a larger scale. Finally, in times where green chemistry and sustainability are top-rated criteria for any chemical process, there is bound to be a major reluctance to apply procedures that cannot guarantee the highest level of environmental concern for both ethical and legal reasons. © 2023 The Author(s)

Place, publisher, year, edition, pages
Cell Press, 2023
National Category
Engineering and Technology
Identifiers
urn:nbn:se:ri:diva-65678 (URN)10.1016/j.xcrp.2023.101493 (DOI)2-s2.0-85165063909 (Scopus ID)
Note

Correspondence Address: H.-J. Federsel; RISE Research Institutes of Sweden, Stockholm, Box 5607, 114 86, Sweden; 

Available from: 2023-08-07 Created: 2023-08-07 Last updated: 2023-10-31Bibliographically approved
Burke, A., Carreiro, E., Amorim, C., Herrman, G., Federsel, H.-J. & Fonseca, D. (2022). Immobilization of Functionalized epi-Cinchonine Organocatalysts on Controlled Porous Glass-Beads: Applications in Batch and Continuous Flow. Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, 33(17), 1756-1762
Open this publication in new window or tab >>Immobilization of Functionalized epi-Cinchonine Organocatalysts on Controlled Porous Glass-Beads: Applications in Batch and Continuous Flow
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2022 (English)In: Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, ISSN 0936-5214, E-ISSN 1437-2096, Vol. 33, no 17, p. 1756-1762Article in journal (Refereed) Published
Abstract [en]

A well-known Squaramide-Cinchonine organocatalyst was immobilized in a controlled way onto three types of commercial porous glass beads EziGTM (EziG OPAL, EziG Amber and EziG Coral) and applied in asymmetric Michael reactions. The performance of the immobilized catalysts was evaluated under batch and continuous flow conditions showing promising results in both approaches. In batch reactions, 0.8 and 1.6 mol% of the immobilized cinchonine-squaramide provided the products with excellent yields (up to 99%) and enantioselectivities (up to 99% ee). These excellent results were also verified in the case of continuous flow reactions, where also 0.8 and 1.6 mol% of the catalyst immobilized onto the glass beads afforded the product with extraordinary yields (up to 99%) and very high enantioselectivities (up to 97% ee). The immobilized catalysts could be recycled (up to 7 cycles) using both approaches. 

Place, publisher, year, edition, pages
Georg Thieme Verlag, 2022
Keywords
Batch reactions, Cinchona alkaloids, Continuous flow reactions, EziGTM, Immobilizations, Organocatalysis
National Category
Biochemistry and Molecular Biology
Identifiers
urn:nbn:se:ri:diva-60064 (URN)10.1055/a-1916-4858 (DOI)2-s2.0-85135752027 (Scopus ID)
Available from: 2022-09-05 Created: 2022-09-05 Last updated: 2023-10-31Bibliographically approved
Burke, A., Federsel, H.-J. & Hermann, G. (2022). Recent Advances in Asymmetric Hydrogenation Catalysis Utilizing Spiro and Other Rigid C-Stereogenic Phosphine Ligands. Journal of Organic Chemistry, 87(4), 1898-1924
Open this publication in new window or tab >>Recent Advances in Asymmetric Hydrogenation Catalysis Utilizing Spiro and Other Rigid C-Stereogenic Phosphine Ligands
2022 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 87, no 4, p. 1898-1924Article in journal (Refereed) Published
Abstract [en]

Transition-metal-catalyzed asymmetric reactions have been a powerful tool in organic synthesis for many years. The design of chiral ligands with the right configuration is fundamental to induce high regio- and stereoselectivity to catalytic reactions and to achieve high turnover numbers and high yields. A challenge is the control of prochiral centers with similar electronic properties in a similar steric environment within the same molecule. Over the last 10 years, a range of novel rigid C-stereogenic chiral phosphine ligands has been developed and successfully applied in various types of asymmetric transformations. Many of these ligands are of a di-, tri-, or multidentate nature. The purpose of this Perspective is to highlight recent synthetic achievements (since 2010) with spiro-phosphines and other rigid phosphines and discuss some mechanistic aspects of the catalytic reactions. 

Place, publisher, year, edition, pages
American Chemical Society, 2022
National Category
Organic Chemistry
Identifiers
urn:nbn:se:ri:diva-56946 (URN)10.1021/acs.joc.1c01571 (DOI)2-s2.0-85117088999 (Scopus ID)
Note

Funding details: Fundação para a Ciência e a Tecnologia, FCT, UIDB/50006/2020; Funding details: European Regional Development Fund, ERDF; Funding details: Programa Operacional Temático Factores de Competitividade, POFC; Funding text 1: A.J.B. thanks FEDER (The European Fund for Regional Development) through the Operational Competitiveness Factors Program – COMPETE and the Foundation for Science and Technology (FCT, Portugal) through project UIDB/50006/2020 for financial support. ChiraTecnics thanks the University of Évora for its support and commitment over the last number of years.

Available from: 2021-11-19 Created: 2021-11-19 Last updated: 2023-10-31Bibliographically approved
Federsel, H.-J. (2022). Taking the Green Road Towards Pharmaceutical Manufacturing. Synthesis (Stuttgart), 54(19), 4257
Open this publication in new window or tab >>Taking the Green Road Towards Pharmaceutical Manufacturing
2022 (English)In: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, Vol. 54, no 19, p. 4257-Article in journal (Refereed) Published
Abstract [en]

The introduction of the Green Chemistry Principles in the late 1990s formed the basis for a transition to a greener environment. These Principles have become an integral part in the work on designing chemical processes, especially for large-scale manufacture. The ultimate target is the achievement of a sustainable production method allowing hundreds of tons of valuable materials to be prepared. For this purpose, a holistic view must be applied to the elements constituting a fullyfledged process encompassing layout of the synthetic route, defining starting materials and their origin, output of product and quality features, quantity of effluent streams and waste, recovery and recycling of chemicals involved, and energy consumption. These parameters form a complex matrix where the individual components are in a complicated relationshipwith each other. This short review addresses these issues and the benefits of life-cycle assessment and metrics commonly used to measure the performance of chemical manufacturing all from a pharmaceutical industry perspective as experienced by the author. 

Place, publisher, year, edition, pages
Georg Thieme Verlag, 2022
Keywords
catalysis, E factor, green chemistry, pharmaceutical manufacturing, PMI, process design, sustainability
National Category
Environmental Sciences
Identifiers
urn:nbn:se:ri:diva-59251 (URN)10.1055/a-1752-5471 (DOI)2-s2.0-85128486434 (Scopus ID)
Available from: 2022-05-23 Created: 2022-05-23 Last updated: 2023-10-31Bibliographically approved
Tran, N., Gelonch, M., Liang, S., Xiao, Z., Sarafraz, M., Tišma, M., . . . Hessel, V. (2021). Enzymatic pretreatment of recycled grease trap waste in batch and continuous-flow reactors for biodiesel production. Chemical Engineering Journal, 426, Article ID 131703.
Open this publication in new window or tab >>Enzymatic pretreatment of recycled grease trap waste in batch and continuous-flow reactors for biodiesel production
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2021 (English)In: Chemical Engineering Journal, ISSN 1385-8947, E-ISSN 1873-3212, Vol. 426, article id 131703Article in journal (Refereed) Published
Abstract [en]

In this study, we investigated enzymatic pre-treatment of grease trap waste (GTW) as an environmentally beneficial procedure for biodiesel production. Different enzymes, both commercial and newly designed industrial enzymes, were used to reduce the free fatty acids (FFA) level of GTW through an esterification reaction. The process conditions were optimized using response surface methodology with central composite design parameters. A set of 30 experiments, for both batch and continuous flow reactors, were designed to identify the optimal process conditions in which the highest conversion of FFA is achieved. Within the range of the selected operating conditions, the optimized values of reaction temperature, catalyst quantities, ethanol to oil molar ratio, and reaction time for the batch reactor, in which FFA level was reduced to 31.5 %, were found to be 70 °C, 4.5 wt%, 3:1, and 25 min respectively. A significant improvement in the reduction of FFA, of which FFA amount is only 9.9 %, was obtained in the flow reactor when using the commercial enzyme (T = 57 °C, catalyst loading 4.85 %, ethanol to oil ratio 2:1, t = 25 min). In addition to achieving higher conversion, the continuous-flow experiments saved time since the entire series of experiments were completed in<1.5 days, compared to the 6 days required for the equivalent batch processes. These results confirm the superiority of the continuous-flow reactors over their batch counterparts and open the door for future automation of the methods.

Place, publisher, year, edition, pages
Elsevier B.V., 2021
Keywords
Biodiesel, Continuous flow reactor, Free fatty acids, Grease trap waste, Lipase, Batch reactors, Esterification, Ethanol, Fatty acids, Lipases, Molar ratio, Waste treatment, Batch flows, Biodiesel production, Continuous flow reactors, Enzymatic pretreatment, Free fatty acid, Grease trap, High conversions, Pre-treatments, Process condition
National Category
Biocatalysis and Enzyme Technology
Identifiers
urn:nbn:se:ri:diva-56667 (URN)10.1016/j.cej.2021.131703 (DOI)2-s2.0-85113605170 (Scopus ID)
Note

Funding details: University of Adelaide; Funding text 1: Dr. Nghiep Nam Tran received financial support from the Start-Up Grant of Professor Volker Hessel at The University of Adelaide. We would also like to thank Peats Soil and Garden Supply Pty. Ltd for providing the GTW samples.; Funding text 2: Dr. Nghiep Nam Tran received financial support from the Start-Up Grant of Professor Volker Hessel at The University of Adelaide. We would also like to thank Peats Soil and Garden Supply Pty. Ltd for providing the GTW samples.

Available from: 2021-11-24 Created: 2021-11-24 Last updated: 2023-10-31Bibliographically approved
Federsel, H.-J., Moody, T. & Taylor, S. (2021). Recent trends in enzyme immobilization—concepts for expanding the biocatalysis toolbox. Molecules, 26(9), Article ID 2822.
Open this publication in new window or tab >>Recent trends in enzyme immobilization—concepts for expanding the biocatalysis toolbox
2021 (English)In: Molecules, ISSN 1431-5157, E-ISSN 1420-3049, Vol. 26, no 9, article id 2822Article in journal (Refereed) Published
Abstract [en]

Enzymes have been exploited by humans for thousands of years in brewing and baking, but it is only recently that biocatalysis has become a mainstream technology for synthesis. Today, enzymes are used extensively in the manufacturing of pharmaceuticals, food, fine chemicals, flavors, fragrances and other products. Enzyme immobilization technology has also developed in parallel as a means of increasing enzyme performance and reducing process costs. The aim of this review is to present and discuss some of the more recent promising technical developments in enzyme immobilization, including the supports used, methods of fabrication, and their application in synthesis. The review highlights new support technologies such as the use of well-established polysaccharides in novel ways, the use of magnetic particles, DNA, renewable materials and hybrid organic–inorganic supports. The review also addresses how immobilization is being integrated into developing biocatalytic technology, for example in flow biocatalysis, the use of 3D printing and multi-enzymatic cascade reactions. © 2021 by the authors. 

Place, publisher, year, edition, pages
MDPI AG, 2021
Keywords
3D-printing, Biocatalysis, Enzyme, Flow processes, Immobilization, Support technologies
National Category
Biocatalysis and Enzyme Technology
Identifiers
urn:nbn:se:ri:diva-53481 (URN)10.3390/molecules26092822 (DOI)2-s2.0-85106286648 (Scopus ID)
Available from: 2021-06-04 Created: 2021-06-04 Last updated: 2023-10-31Bibliographically approved
Federsel, H.-J., Hedberg, M. H., Qvarnström, F. R. & Tian, W. (2013). C-N Coupling Chemistry as a Means to Achieve a Complicated Molecular Architecture: the AR-A2 Case Story. In: Transition Metal-Catalyzed Couplings in Process Chemistry: Case Studies From the Pharmaceutical Industry (pp. 73-89). Wiley-VCH Verlag
Open this publication in new window or tab >>C-N Coupling Chemistry as a Means to Achieve a Complicated Molecular Architecture: the AR-A2 Case Story
2013 (English)In: Transition Metal-Catalyzed Couplings in Process Chemistry: Case Studies From the Pharmaceutical Industry, Wiley-VCH Verlag , 2013, p. 73-89Chapter in book (Other academic)
Abstract [en]

A major drug project in the neuroscience area aimed at designing and developing a viable manufacturing process for AR-A2. This turned out to be a tough challenge that resulted in the use of three different synthetic routes. One step to be included from the very start was a Pd-catalyzed C-N bond formation, and this was retained throughout the later versions of the synthesis. At the time of initiating this project in 1998, the combined Buchwald and Hartwig protocols for effecting the chemistry in question-coupling of a N-containing moiety to an aromatic nucleus had only been known for a few years. Therefore, a lot of experimentation was needed to increase the insight and understanding of the chemistry to optimize the performance to fit for large-scale application. The outcome of the efforts resulted in successfully carrying out the chemical transformation is described in detail in this chapter.

Place, publisher, year, edition, pages
Wiley-VCH Verlag, 2013
Keywords
AR-A2 antagonist, Buchwald-Hartwig coupling, C-N coupling, Chemical transformation, Palladium compounds, Reaction kinetics, Buchwald-hartwig couplings, C-n bond formations, Chemical transformations, Large-scale applications, Manufacturing process, Molecular architecture, Synthetic routes, Chemical bonds
National Category
Engineering and Technology
Identifiers
urn:nbn:se:ri:diva-49932 (URN)10.1002/9783527658909.ch06 (DOI)2-s2.0-84886424882 (Scopus ID)9783527658909 (ISBN)9783527332793 (ISBN)
Available from: 2020-10-29 Created: 2020-10-29 Last updated: 2023-10-31Bibliographically approved
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ORCID iD: ORCID iD iconorcid.org/0000-0001-5781-1689

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