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Publications (10 of 39) Show all publications
Li, L., Das, B., Rahaman, A., Shatskiy, A., Ye, F., Cheng, P., . . . Åkermark, B. (2022). Ruthenium containing molecular electrocatalyst on glassy carbon for electrochemical water splitting. Dalton Transactions, 51(20), 7957-7965
Open this publication in new window or tab >>Ruthenium containing molecular electrocatalyst on glassy carbon for electrochemical water splitting
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2022 (English)In: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, Vol. 51, no 20, p. 7957-7965Article in journal (Refereed) Published
Abstract [en]

Electrochemical water splitting constitutes one of the most promising strategies for converting water into hydrogen-based fuels, and this technology is predicted to play a key role in the transition towards a carbon-neutral energy economy. To enable the design of cost-effective electrolysis cells based on this technology, new and more efficient anodes with augmented water splitting activity and stability will be required. Herein, we report an active molecular Ru-based catalyst for electrochemically-driven water oxidation (overpotential of ∼395 mV at pH 7 phosphate buffer) and two simple methods for preparing anodes by attaching this catalyst onto glassy carbon through multi-walled carbon nanotubes to improve stability as well as reactivity. The anodes modified with the molecular catalyst were characterized by a broad toolbox of microscopy and spectroscopy techniques, and interestingly no RuO2 formation was detected during electrocatalysis over 4 h. These results demonstrate that the herein presented strategy can be used to prepare anodes that rival the performance of state-of-the-art metal oxide anodes.

National Category
Chemical Sciences
Identifiers
urn:nbn:se:su:diva-205241 (URN)10.1039/d2dt00824f (DOI)000793892800001 ()35546321 (PubMedID)
Available from: 2022-06-01 Created: 2022-06-01 Last updated: 2022-06-01Bibliographically approved
Pourghasemi Lati, M., Ståhle, J., Meyer, M. & Verho, O. (2021). A Study of an 8-Aminoquinoline-Directed C(sp2)–H Arylation Reaction on the Route to Chiral Cyclobutane Keto Acids from Myrtenal. Journal of Organic Chemistry, 86(12), 8527-8537
Open this publication in new window or tab >>A Study of an 8-Aminoquinoline-Directed C(sp2)–H Arylation Reaction on the Route to Chiral Cyclobutane Keto Acids from Myrtenal
2021 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 86, no 12, p. 8527-8537Article in journal (Refereed) Published
Abstract [en]

This work outlines a synthetic route that can be used to access chiral cyclobutane keto acids with two stereocenters in five steps from the inexpensive terpene myrtenal. Furthermore, the developed route includes an 8-aminoquinoline-directed C(sp2)–H arylation as one of its key steps, which allows a wide range of aryl and heteroaryl groups to be incorporated into the bicyclic myrtenal scaffold prior to the ozonolysis-based ring-opening step that furnishes the target cyclobutane keto acids. This synthetic route is expected to find many applications connected to the synthesis of natural product-like compounds and small molecule libraries.

National Category
Chemical Sciences
Identifiers
urn:nbn:se:su:diva-196525 (URN)10.1021/acs.joc.1c00774 (DOI)000664332300056 ()34042431 (PubMedID)
Available from: 2021-09-07 Created: 2021-09-07 Last updated: 2022-02-25Bibliographically approved
Yuan, N., Gudmundsson, A., Gustafson, K. P. J., Oschmann, M., Tai, C.-W., Persson, I., . . . Bäckvall, J.-E. (2021). Investigation of the Deactivation and Reactivation Mechanism of a Heterogeneous Palladium(II) Catalyst in the Cycloisomerization of Acetylenic Acids by In Situ XAS. ACS Catalysis, 11(5), 2999-3008
Open this publication in new window or tab >>Investigation of the Deactivation and Reactivation Mechanism of a Heterogeneous Palladium(II) Catalyst in the Cycloisomerization of Acetylenic Acids by In Situ XAS
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2021 (English)In: ACS Catalysis, E-ISSN 2155-5435, Vol. 11, no 5, p. 2999-3008Article in journal (Refereed) Published
Abstract [en]

A well-studied heterogeneous palladium(II) catalyst used for the cycloisomerization of acetylenic acids is known to be susceptible to deactivation through reduction. To gain a deeper understanding of this deactivation process and to enable the design of a reactivation strategy, in situ X-ray absorption spectroscopy (XAS) was used. With this technique, changes in the palladium oxidation state and coordination environment could be studied in close detail, which provided experimental evidence that the deactivation was primarily caused by triethylamine-promoted reduction of palladium(II) to metallic palladium nanoparticles. Furthermore, it was observed that the choice of the acetylenic acid substrate influenced the distribution between palladium(II) and palladium(0) species in the heterogeneous catalyst after the reaction. From the mechanistic insight gained through XAS, an improved catalytic protocol was developed that did not suffer from deactivation and allowed for more efficient recycling of the catalyst.

Keywords
X-ray absorption spectroscopy, cycloisomerization, deactivation/reactivation, heterogeneous, palladium catalysis
National Category
Chemical Sciences
Identifiers
urn:nbn:se:su:diva-193379 (URN)10.1021/acscatal.0c04374 (DOI)000626844200049 ()33842022 (PubMedID)
Available from: 2021-05-26 Created: 2021-05-26 Last updated: 2024-07-04Bibliographically approved
Verho, O. & Bäckvall, J.-E. (2020). Nanocatalysis Meets Biology (1ed.). In: Shū Kobayashi (Ed.), Nanoparticles in Catalysis: (pp. 243-278). Cham: Springer, 66
Open this publication in new window or tab >>Nanocatalysis Meets Biology
2020 (English)In: Nanoparticles in Catalysis / [ed] Shū Kobayashi, Cham: Springer, 2020, 1, Vol. 66, p. 243-278Chapter in book (Refereed)
Abstract [en]

This chapter will review the currently available strategies for interfacing transition metal nanoparticles with enzymes and other more complex biological systems, as well as the applications of such biometal hybrids in the areas of catalysis, energy production, environmental remediation, and medicine. In the first part of this chapter, the focus will be on the many nanometal-enzyme hybrids that have been developed for applications in organic synthesis. Within the field of organic chemistry, nanometal-enzyme hybrids are often used as bifunctional catalysts to mediate different multistep transformations, as for example the dynamic kinetic resolution of alcohols and amines. The second part of this chapter will offer an overview of nanometal-enzyme hybrids that are used as bioelectrodes in biofuel cells. This area of research has grown significantly during the past decades, much because of the many potential future applications of such devices for medical purposes. Here, nanometal-enzyme hybrid based biofuel cells hold particular promise for biosensing applications, as well as for replacing battery-based solutions in actuator devices such as mechanical valves and pacemakers. In the final part of this chapter, the different strategies to use bacteria to synthesize metal nanoparticles will be reviewed. As will be shown by the many examples in this part, biologically synthesized and supported transition metal nanoparticles constitute interesting catalytic systems that could for example be used for energy production, pollutant degradation, and small molecule synthesis.

Place, publisher, year, edition, pages
Cham: Springer, 2020 Edition: 1
Series
Topics in Organometallic Chemistry, ISSN 1436-6002, E-ISSN 1616-8534 ; 66
Keywords
catalysis, nanoparticles, nanometal-enzyme hybrids, biofuel cells, biosynthesis
National Category
Chemical Sciences
Identifiers
urn:nbn:se:su:diva-191302 (URN)10.1007/3418_2020_38 (DOI)000608805900008 ()978-3-030-56632-6 (ISBN)978-3-030-56629-6 (ISBN)978-3-030-56630-2 (ISBN)
Available from: 2021-03-26 Created: 2021-03-26 Last updated: 2022-02-25Bibliographically approved
Oschmann, M., Johansson Holm, L., Pourghasemi-Lati, M. & Verho, O. (2020). Synthesis of Elaborate Benzofuran-2-Carboxamide Derivatives through a Combination of 8-Aminoquinoline Directed C–H Arylation and Transamidation Chemistry. Molecules, 25(2), Article ID 361.
Open this publication in new window or tab >>Synthesis of Elaborate Benzofuran-2-Carboxamide Derivatives through a Combination of 8-Aminoquinoline Directed C–H Arylation and Transamidation Chemistry
2020 (English)In: Molecules, ISSN 1431-5157, E-ISSN 1420-3049, Vol. 25, no 2, article id 361Article in journal (Refereed) Published
Abstract [en]

Herein, we present a short and highly modular synthetic route that involves 8-aminoquinoline directed C–H arylation and transamidation chemistry, and which enables access to a wide range of elaborate benzofuran-2-carboxamides. For the directed C–H arylation reactions, Pd catalysis was used to install a wide range of aryl and heteroaryl substituents at the C3 position of the benzofuran scaffold in high efficiency. Directing group cleavage and further diversification of the C3-arylated benzofuran products were then achieved in a single synthetic operation through the utilization of a one-pot, two-step transamidation procedure, which proceeded via the intermediate N-acyl-Boc-carbamates. Given the high efficiency and modularity of this synthetic strategy, it constitutes a very attractive method for generating structurally diverse collections of benzofuran derivatives for small molecule screening campaigns.

Keywords
palladium, C–H functionalization, 8-aminoquinoline, benzofuran, transamidation
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-180978 (URN)10.3390/molecules25020361 (DOI)000515381800123 ()
Available from: 2020-04-22 Created: 2020-04-22 Last updated: 2023-08-28Bibliographically approved
Schmitz, A. J., Ricke, A., Oschmann, M. & Verho, O. (2019). Convenient Access to Chiral Cyclobutanes with Three Contiguous Stereocenters from Verbenone by Directed C(sp(3))-H arylation. Chemistry - A European Journal, 25(20), 5154-5157
Open this publication in new window or tab >>Convenient Access to Chiral Cyclobutanes with Three Contiguous Stereocenters from Verbenone by Directed C(sp(3))-H arylation
2019 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 25, no 20, p. 5154-5157Article in journal (Refereed) Published
Abstract [en]

This work demonstrates how a series of complex, chiral cyclobutane derivatives can be accessed in four steps from the terpene verbenone through the application of a directed C-H functionalization approach. The developed synthetic route involved an 8-aminoquinoline-directed C(sp(3))-H arylation as the key step, and this reaction could be carried out with a wide range of aryl and heteroaryl iodides to furnish a variety of cyclobutane products with three contiguous stereocenters. Moreover, it was shown that the 8-aminoquinoline auxiliary could be effectively removed from the cyclobutane derivatives using an ozonolysis-based cleavage method.

Keywords
8-aminoquinoline, C(sp(3))-H functionalization, cyclobutanes, palladium, verbenone
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-170158 (URN)10.1002/chem.201806416 (DOI)000468855200007 ()30716181 (PubMedID)
Available from: 2019-06-25 Created: 2019-06-25 Last updated: 2022-02-26Bibliographically approved
Oschmann, M., Placais, C., Nagendiran, A., Bäckvall, J.-E. & Verho, O. (2019). Efficient 1,3-Oxazolidin-2-one Synthesis through Heterogeneous Pd-II-Catalyzed Intramolecular Hydroamination of Propargylic Carbamates. Chemistry - A European Journal, 25(25), 6295-6299
Open this publication in new window or tab >>Efficient 1,3-Oxazolidin-2-one Synthesis through Heterogeneous Pd-II-Catalyzed Intramolecular Hydroamination of Propargylic Carbamates
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2019 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 25, no 25, p. 6295-6299Article in journal (Refereed) Published
Abstract [en]

Herein, we present an operationally simple protocol for the cycloisomerization of propargylic carbamates in which a heterogeneous catalyst consisting of Pd species immobilized on amino-functionalized siliceous mesocellular foam (Pd-II-AmP-MCF) is used. This Pd nanocatalyst displayed high efficiency at low catalyst loading and reaction temperatures, which allowed for the efficient and mild synthesis of a wide range of 1,3-oxazolidin-2-one derivatives and related compounds. Moreover, it proved possible to re-use the Pd nanocatalyst for several reactions, although a gradual decrease in activity was observed in the subsequent cycles.

Keywords
cycloisomerization, heterogeneous catalysis, mesoporous silica, oxazolidinones, palladium
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-171163 (URN)10.1002/chem.201900678 (DOI)000471033900007 ()30888694 (PubMedID)
Available from: 2019-08-08 Created: 2019-08-08 Last updated: 2022-02-26Bibliographically approved
Yuan, N., Guðmundsson, A., Gustafson, K., Oschmann, M., Verho, O., Zou, X., . . . Bäckvall, J.-E. (2019). In Situ XAS Investigation of the Deactivation and Reactivation Mechanisms of a Heterogeneous Palladium(II) catalyst during the Cycloisomerization of Acetylenic Acids.
Open this publication in new window or tab >>In Situ XAS Investigation of the Deactivation and Reactivation Mechanisms of a Heterogeneous Palladium(II) catalyst during the Cycloisomerization of Acetylenic Acids
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2019 (English)Manuscript (preprint) (Other academic)
Abstract [en]

The cause and mechanism of deactivation of a well-studied heterogeneous palladium(II) catalyst in the intramolecular lactonization of acetylenic acids to γ-alkylidene lactones have been investigated. It was shown that the deactivation was driven by the formation of reduced palladium species following the addition of the base triethylamine. In this work, X-ray absorption spectroscopy (XAS) was used to identify the palladium species and follow their evolution over the course of the reaction. It was also found that the choice of substrates has significant influences on the Pd species under the same reaction conditions. With these insights into the deactivation mechanism derived from XAS, different strategies were tested and illustrated to regain or maintain the active state of the catalyst. This information was further used to develop a new protocol, which can effectively prevent the deactivation of the catalyst and prolong its usage. 

National Category
Chemical Sciences
Research subject
Inorganic Chemistry; Organic Chemistry
Identifiers
urn:nbn:se:su:diva-167289 (URN)
Available from: 2019-03-26 Created: 2019-03-26 Last updated: 2022-02-26Bibliographically approved
Verho, O., Pourghasemi Lati, M. & Oschmann, M. (2018). A Two-Step Procedure for the Overall Transamidation of 8-Aminoquinoline Amides Proceeding via the Intermediate N-Acyl-Boc-Carbamates. Journal of Organic Chemistry, 83(8), 4464-4476
Open this publication in new window or tab >>A Two-Step Procedure for the Overall Transamidation of 8-Aminoquinoline Amides Proceeding via the Intermediate N-Acyl-Boc-Carbamates
2018 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 83, no 8, p. 4464-4476Article in journal (Refereed) Published
Abstract [en]

Herein a two-step strategy for achieving overall transamidation of 8-aminoquinoline amides has been explored. In this protocol, the 8-aminoquinoline amides were first treated with Boc(2)O and DMAP to form the corresponding N-acyl-Boc-carbamates, which were found to be sufficiently reactive to undergo subsequent aminolysis with different amines in the absence of any additional reagents or catalysts. To demonstrate the utility of this approach, it was applied on a number of 8-aminoquinoline amides from the recent C-H functionalization literature, enabling access to a range of elaborate amide derivatives in good to high yields

National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:su:diva-156672 (URN)10.1021/acs.joc.8b00174 (DOI)000430898500015 ()29578345 (PubMedID)
Available from: 2018-06-01 Created: 2018-06-01 Last updated: 2022-02-26Bibliographically approved
Ibrahem, I., Iqbal, M. N., Verho, O., Eivazihollagh, A., Olsén, P., Edlund, H., . . . Johnston, E. V. (2018). Copper Nanoparticles on Controlled Pore Glass and TEMPO for the Aerobic Oxidation of Alcohols. ChemNanoMat, 4(1), 71-75
Open this publication in new window or tab >>Copper Nanoparticles on Controlled Pore Glass and TEMPO for the Aerobic Oxidation of Alcohols
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2018 (English)In: ChemNanoMat, E-ISSN 2199-692X, Vol. 4, no 1, p. 71-75Article in journal (Refereed) Published
Abstract [en]

Herein, we report on the facile synthesis of a heterogeneous copper nanocatalyst and its combination with 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) for the aerobic oxidation of alcohols to their corresponding carbonyl compounds. This low cost copper nanocatalyst was found to exhibit excellent recyclability, making it a highly attractive catalytic system from an economical and environmental point of view. Extensive characterization of the catalyst by a number of techniques revealed that it was comprised of well-dispersed Cu(I/II) nanoparticles with an average size of around 6nm.

Keywords
alcohol oxidation, copper nanoparticles, green chemistry, heterogeneous catalysis, TEMPO
National Category
Chemical Sciences Nano Technology Materials Engineering
Identifiers
urn:nbn:se:su:diva-152590 (URN)10.1002/cnma.201700309 (DOI)000419237800011 ()
Available from: 2018-02-06 Created: 2018-02-06 Last updated: 2023-03-28Bibliographically approved
Organisations
Identifiers
ORCID iD: ORCID iD iconorcid.org/0000-0002-3153-748x

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