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  1. Article ; Online: Gas Evolution as a Tool to Study Reaction Kinetics Under Biomimetic Conditions.

    Meeus, Eva J / Laan, Petrus C M / Ham, Rens / de Bruin, Bas / Reek, Joost N H

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2024  Volume 30, Issue 23, Page(s) e202400516

    Abstract: The field of bioorthogonal chemistry is rapidly growing, presenting successful applications of organic and transition metal-catalysed reactions in cells and living systems (in vivo). The development of such reactions typically proceeds through many ... ...

    Abstract The field of bioorthogonal chemistry is rapidly growing, presenting successful applications of organic and transition metal-catalysed reactions in cells and living systems (in vivo). The development of such reactions typically proceeds through many iterative steps focused on biocompatibility and fast reaction kinetics to ensure product formation. However, obtaining kinetic data, even under simulated biological (biomimetic) conditions, remains a challenge due to substantial concentrations of salts and biomolecules hampering the use of typically employed solution-phase analytical techniques. In this study, we explored the suitability of gas evolution as a probe to study kinetics under biomimetic conditions. As proof of concept, we show that the progress of two transition metal-catalysed bioorthogonal chemical reactions can be accurately monitored, regardless of the complexity of the medium. As such, we introduce a protocol to gain more insight into the performance of a catalytic system under biomimetic conditions to further progress iterative catalyst development for in vivo applications.
    MeSH term(s) Catalysis ; Kinetics ; Biomimetics/methods ; Gases/chemistry ; Transition Elements/chemistry ; Biomimetic Materials/chemistry
    Chemical Substances Gases ; Transition Elements
    Language English
    Publishing date 2024-03-14
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.202400516
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  2. Article ; Online: Transition Metal Catalysis in Living Cells: Progress, Challenges, and Novel Supramolecular Solutions.

    James, Catriona C / de Bruin, Bas / Reek, Joost N H

    Angewandte Chemie (International ed. in English)

    2023  Volume 62, Issue 41, Page(s) e202306645

    Abstract: The importance of transition metal catalysis is exemplified by its wide range of applications, for example in the synthesis of chemicals, natural products, and pharmaceuticals. However, one relatively new application is for carrying out new-to-nature ... ...

    Abstract The importance of transition metal catalysis is exemplified by its wide range of applications, for example in the synthesis of chemicals, natural products, and pharmaceuticals. However, one relatively new application is for carrying out new-to-nature reactions inside living cells. The complex environment of a living cell is not welcoming to transition metal catalysts, as a diverse range of biological components have the potential to inhibit or deactivate the catalyst. Here we review the current progress in the field of transition metal catalysis, and evaluation of catalysis efficiency in living cells and under biological (relevant) conditions. Catalyst poisoning is a ubiquitous problem in this field, and we propose that future research into the development of physical and kinetic protection strategies may provide a route to improve the reactivity of catalysts in cells.
    MeSH term(s) Transition Elements/chemistry ; Catalysis
    Chemical Substances Transition Elements
    Language English
    Publishing date 2023-07-07
    Publishing country Germany
    Document type Journal Article ; Review
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.202306645
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  3. Article: Carbene Radicals in Transition-Metal-Catalyzed Reactions.

    Epping, Roel F J / Vesseur, David / Zhou, Minghui / de Bruin, Bas

    ACS catalysis

    2023  Volume 13, Issue 8, Page(s) 5428–5448

    Abstract: Discovered as organometallic curiosities in the 1970s, carbene radicals have become a staple in modern-day homogeneous catalysis. Carbene radicals exhibit nucleophilic radical-type reactivity orthogonal to classical electrophilic diamagnetic Fischer ... ...

    Abstract Discovered as organometallic curiosities in the 1970s, carbene radicals have become a staple in modern-day homogeneous catalysis. Carbene radicals exhibit nucleophilic radical-type reactivity orthogonal to classical electrophilic diamagnetic Fischer carbenes. Their successful catalytic application has led to the synthesis of a myriad of carbo- and heterocycles, ranging from simple cyclopropanes to more challenging eight-membered rings. The field has matured to employ densely functionalized chiral porphyrin-based platforms that exhibit high enantio-, regio-, and stereoselectivity. Thus far the focus has largely been on cobalt-based systems, but interest has been growing for the past few years to expand the application of carbene radicals to other transition metals. This Perspective covers the advances made since 2011 and gives an overview on the coordination chemistry, reactivity, and catalytic application of carbene radical species using transition metal complexes and catalysts.
    Language English
    Publishing date 2023-04-06
    Publishing country United States
    Document type Journal Article ; Review
    ISSN 2155-5435
    ISSN 2155-5435
    DOI 10.1021/acscatal.3c00591
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  4. Article ; Online: Cobalt-Catalyzed Asymmetric Hydrogenation: Substrate Specificity and Mechanistic Variability.

    Chakrabortty, Soumyadeep / de Bruin, Bas / de Vries, Johannes G

    Angewandte Chemie (International ed. in English)

    2023  Volume 63, Issue 10, Page(s) e202315773

    Abstract: Asymmetric hydrogenation finds widespread application in academia and industry. And indeed, a number of processes have been implemented for the production of pharma and agro intermediates as well as flavors & fragrances. Although these processes are all ... ...

    Abstract Asymmetric hydrogenation finds widespread application in academia and industry. And indeed, a number of processes have been implemented for the production of pharma and agro intermediates as well as flavors & fragrances. Although these processes are all based on the use of late transition metals as catalysts, there is an increasing interest in the use of base metal catalysis in view of their lower cost and the expected different substrate scope. Catalysts based on cobalt have already shown their potential in enantioselective hydrogenation chemistry. This review outlines the impressive progress made in recent years on cobalt-catalyzed asymmetric hydrogenation of different unsaturated substrates. We also illustrate the ligand dependent substrate specificity as well as the mechanistic variability in detail. This may well guide further catalyst development in this research area.
    Language English
    Publishing date 2023-12-19
    Publishing country Germany
    Document type Journal Article ; Review
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.202315773
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  5. Article ; Online: Thermal and (Thermo-Reversible) Photochemical Cycloisomerization of 1

    Zhou, Minghui / Mathew, Simon / de Bruin, Bas

    Journal of the American Chemical Society

    2022  Volume 145, Issue 1, Page(s) 645–657

    Abstract: A novel T-type molecular photoswitch based on the reversible cyclization of ... ...

    Abstract A novel T-type molecular photoswitch based on the reversible cyclization of 1
    MeSH term(s) Molecular Structure ; Oxocins ; Cyclization ; Solvents
    Chemical Substances Oxocins ; Solvents
    Language English
    Publishing date 2022-12-22
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/jacs.2c11310
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  6. Article ; Online: Photoactive Fe Catalyst for Light-Triggered Alkyd Paint Curing.

    Bootsma, Johan / Browne, Wesley R / Flapper, Jitte / de Bruin, Bas

    JACS Au

    2022  Volume 2, Issue 2, Page(s) 531–540

    Abstract: Herein, we show that the photoactive complexes [(Cp)Fe(arene)] ...

    Abstract Herein, we show that the photoactive complexes [(Cp)Fe(arene)]
    Language English
    Publishing date 2022-01-27
    Publishing country United States
    Document type Journal Article
    ISSN 2691-3704
    ISSN (online) 2691-3704
    DOI 10.1021/jacsau.1c00579
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  7. Article ; Online: C-H Bond Activation by Iridium(III) and Iridium(IV) Oxo Complexes.

    Tepaske, Martijn A / Fitterer, Arnd / Verplancke, Hendrik / Delony, Daniel / Neben, Marc C / de Bruin, Bas / Holthausen, Max C / Schneider, Sven

    Angewandte Chemie (International ed. in English)

    2024  Volume 63, Issue 7, Page(s) e202316729

    Abstract: Oxidation of an iridium(III) oxo precursor enabled the structural, spectroscopic, and quantum-chemical characterization of the first well-defined iridium(IV) oxo complex. Side-by-side examination of the proton-coupled electron transfer thermochemistry ... ...

    Abstract Oxidation of an iridium(III) oxo precursor enabled the structural, spectroscopic, and quantum-chemical characterization of the first well-defined iridium(IV) oxo complex. Side-by-side examination of the proton-coupled electron transfer thermochemistry revealed similar driving forces for the isostructural oxo complexes in two redox states due to compensating contributions from H
    Language English
    Publishing date 2024-01-10
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.202316729
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  8. Article ; Online: Copper-Catalyzed Sulfimidation in Aqueous Media: a Fast, Chemoselective and Biomolecule-Compatible Reaction.

    Meeus, Eva J / Álvarez, María / Koelman, Emma / Pérez, Pedro J / Reek, Joost N H / de Bruin, Bas

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2024  Volume 30, Issue 14, Page(s) e202303939

    Abstract: Performing transition metal-catalyzed reactions in cells and living systems has equipped scientists with a toolbox to study biological processes and release drugs on demand. Thus far, an impressive scope of reactions has been performed in these settings, ...

    Abstract Performing transition metal-catalyzed reactions in cells and living systems has equipped scientists with a toolbox to study biological processes and release drugs on demand. Thus far, an impressive scope of reactions has been performed in these settings, but many are yet to be introduced. Nitrene transfer presents a rather unexplored new-to-nature reaction. The reaction products are frequently encountered motifs in pharmaceuticals, presenting opportunities for the controlled, intracellular synthesis of drugs. Hence, we explored the transition metal-catalyzed sulfimidation reaction in water for future in vivo application. Two Cu(I) complexes containing trispyrazolylborate ligands (Tp
    Language English
    Publishing date 2024-01-17
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.202303939
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  9. Article ; Online: N-Heterocyclic Carbene Analogues of Wittig Hydrocarbon.

    Steffenfauseweh, Henric / Vishnevskiy, Yury V / Neumann, Beate / Stammler, Hans-Georg / de Bruin, Bas / Ghadwal, Rajendra S

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2024  , Page(s) e202400879

    Abstract: N-Heterocyclic carbene (NHC) analogues of Wittig hydrocarbon, [(NHC)(Stil)(NHC)] (3a-c) (NHC = SIPr (1a) = C[N(Dipp) ... ...

    Abstract N-Heterocyclic carbene (NHC) analogues of Wittig hydrocarbon, [(NHC)(Stil)(NHC)] (3a-c) (NHC = SIPr (1a) = C[N(Dipp)CH
    Language English
    Publishing date 2024-03-04
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.202400879
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  10. Article ; Online: Iron-Catalyzed Intermolecular C-N Cross-Coupling Reactions via Radical Activation Mechanism.

    Das, Subrata / Ehlers, Andreas W / Patra, Sima / de Bruin, Bas / Chattopadhyay, Buddhadeb

    Journal of the American Chemical Society

    2023  Volume 145, Issue 27, Page(s) 14599–14607

    Abstract: A concept for intermolecular C-N cross-coupling amination has been discovered using tetrazoles and aromatic and aliphatic azides with boronic acids under iron-catalyzed conditions. The amination follows an unprecedented metalloradical activation ... ...

    Abstract A concept for intermolecular C-N cross-coupling amination has been discovered using tetrazoles and aromatic and aliphatic azides with boronic acids under iron-catalyzed conditions. The amination follows an unprecedented metalloradical activation mechanism that is different from traditional metal-catalyzed C-N cross-coupling reactions. The scope of the reaction has been demonstrated by the employment of a large number of tetrazoles, azides, and boronic acids. Moreover, several late-stage aminations and a short synthesis of a drug candidate have been showcased for further synthetic utility. Collectively, this iron-catalyzed C-N cross-coupling should have wide applications in the context of medicinal chemistry, drug discovery, and pharmaceutical industries.
    Language English
    Publishing date 2023-06-30
    Publishing country United States
    Document type Journal Article
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/jacs.3c05627
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