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  • 1. Das, Biswanath
    et al.
    Lee, Bao-Lin
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Karlsson, Erik A.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Åkermark, Torbjörn
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Shatskiy, Andrey
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Demeshko, Serhiy
    Liao, Rong-Zhen
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Laine, Tanja M.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Haukka, Matti
    Zeglio, Erica
    Abdel-Magied, Ahmed F.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi. Nuclear Materials Authority, Egypt.
    Siegbahn, Per E. M.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Meyer, Franc
    Kärkäs, Markus D.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Johnston, Eric V.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Nordlander, Ebbe
    Åkermark, Björn
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Water oxidation catalyzed by molecular di- and nonanuclear Fe complexes: importance of a proper ligand framework2016Inngår i: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, Vol. 45, nr 34, s. 13289-13293Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The synthesis of two molecular iron complexes, a dinuclear iron(III,III) complex and a nonanuclear iron complex, based on the di-nucleating ligand 2,2'-(2-hydroxy-5-methyl-1,3-phenylene)bis(1H-benzo[d]imidazole-4-carboxylic acid) is described. The two iron complexes were found to drive the oxidation of water by the one-electron oxidant [Ru(bpy)(3)](3+).

  • 2.
    Johnston, Eric V
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Karlsson, Erik A
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Kärkäs, Markus
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Lee, Bao-Lin
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Åkermark, Björn
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Novel dinuclear Ru-complex for water oxidation2010Inngår i: Abstracts of Papers, 240th ACS National Meeting, Boston, MA, United States, August 22-26, 2010 (2010), American Chemical Society , 2010Konferansepaper (Annet vitenskapelig)
  • 3.
    Johnston, Eric V.
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Karlsson, Erik A.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Lindberg, Staffan A.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Åkermark, Björn
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-E.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Efficient reoxidation of palladium by a hybrid catalyst in aerobic palladium-catalyzed carbocyclization of enallenes2009Inngår i: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 15, nr 28, s. 6799-6801Artikkel i tidsskrift (Fagfellevurdert)
  • 4.
    Johnston, Eric V.
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Karlsson, Erik A.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Tran, Lien-Hoa
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Åkermark, Björn
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-E.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Efficient aerobic ruthenium-catalyzed oxidation of secondary alcohols by the use of a hybrid electron transfer catalyst2010Inngår i: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, nr 10, s. 1971-1976Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Biomimetic aerobic oxidation of secondary alcohols has been performed using hybrid catalyst 1 and Shvo's catalyst 2. This combination allows mild reaction conditions and low catalytic loading, due to the efficiency of intramolecular electron transfer. By this method a wide range of different alcohols have been converted into their corresponding ketones. Oxidation of benzylic as well as aliphatic, electron-rich, electron-deficient and sterically hindered alcohols could be oxidized in excellent yield and selectivity. Oxidation of (S)-1-phenyl-ethanol showed that no racemization occurred during the course of the reaction, indicating that the hydride 2b adds to the quinone much faster than it re-adds to the ketone product. The kinetic deuterium isotope effect of the oxidation was determined by the use of 1-phenylethanol (3a) and 1-deuterio-1-phenylethanol (3a-d1) in parallel and competitive manner, which gave the same isotope effect within experimental error (k(H)/k(D) approximate to 2.8). This indicates that there is no strong coordination of the substrate to the catalyst.

  • 5.
    Johnston, Eric V.
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Karlsson, Erik A.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Tran, Lien-Hoa
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Åkermark, Björn
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-E.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Efficient synthesis of hybrid (hydroquinone-Schiff base)cobalt oxidation catalysts2009Inngår i: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, nr 23, s. 3973-3976Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Hybrid catalysts A and B have recently been found to efficiently transfer electrons from a metal catalyst to molecular oxygen in biomimetic oxidations. In the present work hybrid catalysts A and B were synthesized in high yield from inexpensive starting materials. The key step is an efficient Suzuki cross-coupling, which allows the use of unprotected aldehyde 5. The new synthesis of the title hybrid catalysts is easy to carry out and can be scaled up.

  • 6.
    Karlsson, Erik
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Catalysts for Oxygen Production and Utilization: Closing the Oxygen Cycle: From Biomimetic Oxidation to Artificial Photosynthesis2011Doktoravhandling, med artikler (Annet vitenskapelig)
    Abstract [en]

    This thesis describes the development and study of catalysts for redox reactions, which either utilize oxygen or hydrogen peroxide for the purpose of selectively oxidizing organic substrates, or produce oxygen as the necessary byproduct in the production of hydrogen by artificial photosynthesis.

    The first chapter gives a general introduction about the use of environmentally friendly oxidants in the field of organic synthesis, and about the field of artificial photosynthesis. The second chapter describes a computational study of the mechanism of palladium-catalyzed oxidative carbohydroxylation of allene-substituted conjugated dienes. The proposed mechanism, which was supported by DFT calculations, involves an unusual water attack on a (π-allyl)palladium complex. The third chapter describes a computational study of the oxidation of unfunctionalized hydrocarbons, ethers and alcohols with hydrogen peroxide, catalyzed by methyltrioxorhenium (MTO). The mechanism was found to proceed via rate-limiting hydride abstraction followed by hydroxide transfer in a single concerted, but highly asynchronous, step as shown by intrinsic reaction coordinate (IRC) scans. The fourth chapter describes the use of a new hybrid (hydroquinone-Schiff base)cobalt catalyst as electron transfer mediator (ETM) in the palladium-catalyzed aerobic carbocyclization of enallenes. Covalently linking the two ETMs gave a fivefold rate increase compared to the use of separate components. The fifth chapter describes an improved synthetic route to the (hydroquinone-Schiff base)cobalt catalysts. Preparation of the key intermediate 5-(2,5-hydroxyphenyl)salicylaldehyde was improved by optimization of the key Suzuki coupling and change of protecting groups from methyl ethers to easily cleaved THP groups. The catalysts could thus be prepared in good overall yield from inexpensive starting materials.

    Finally, the sixth chapter describes the preparation and study of two catalysts for water oxidation, both based on ligands containing imidazole groups, analogous to the histidine residues present in the oxygen evolving complex (OEC) and in many other metalloenzymes. The first, ruthenium-based, catalyst was found to catalyze highly efficient water oxidation induced by visible light. The second catalyst is, to the best of our knowledge, the first homogeneous manganese complex to catalyze light-driven water oxidation.

    Fulltekst (pdf)
    FULLTEXT01
  • 7.
    Karlsson, Erik
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Catalytic Oxidation Methods. Use of inexpensive and environmentally friendly Oxidants in organic Synthesis.2009Licentiatavhandling, med artikler (Annet vitenskapelig)
  • 8.
    Karlsson, Erik A.
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-E.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Mechanism of the palladium-catalyzed carbohydroxylation of allene-substituted conjugated dienes: rationalization of the recently observed nucleophilic attack by water on a (pi-allyl)palladium intermediate2008Inngår i: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 14, nr 30, s. 9175-9180Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The mechanism of the palladium-catalyzed oxidative carbohydroxylation of allene-substituted 1,3-cyclohexadiene was studied by DFT calculations. All intermediates and transition states of the reaction were identified and their structures were calculated. The calculations confirm the mechanism previously proposed and show that the CC bond-forming step occurs via insertion of one of the double bonds of 1,3-cyclohexadiene into a Pdvinyl bond of a vinylpalladium intermediate. This reaction leads to a (π-allyl)palladium intermediate, and coordination of benzoquinone and a double bond in the molecule to Pd creates a highly reactive cationic π-allyl complex, which is readily attacked by water according to the calculations.

  • 9.
    Karlsson, Erik A.
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Lee, Bao-Lin
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Åkermark, Torbjörn
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för material- och miljökemi (MMK).
    Johnston, Eric V.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Kärkäs, Markus D.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Sun, Junliang
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för material- och miljökemi (MMK).
    Hansson, Örjan
    Bäckvall, Jan-E.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Åkermark, Björn
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Photosensitized water oxidation by use of a bioinspired manganese catalyst2011Inngår i: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 50, nr 49, s. 11715-11718Artikkel i tidsskrift (Fagfellevurdert)
  • 10.
    Karlsson, Erik A.
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Privalov, Timofei
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Oxidation of ethers, alcohols, and unfunctionalized hydrocarbons by the methyltrioxorhenium/H2O2 system: a computational study on catalytic C-H bond activation2009Inngår i: Abstracts of Papers, 238th ACS National Meeting, Washington, DC, United States, August 16-20, 2009, Washington DC: American Chemical Society , 2009Konferansepaper (Annet vitenskapelig)
  • 11.
    Karlsson, Erik A.
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Privalov, Timofei
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Oxidation of ethers, alcohols, and unfunctionalized hydrocarbons by the methyltrioxorhenium/H2O2 system: a computational study on catalytic C-H bond activation2009Inngår i: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 15, nr 8, s. 1862-1869Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A concerted mechanism that does not involve an ionic intermediate was revealed by a DFT study on oxidation of ethers, alcohols, and unfunctionalized hydrocarbons by methyltrioxorhenium/H2O2. Instead, CH insertion occurs through hydride transfer and then turns into a hydroxide transfer/rebound in a concerted fashion. The picture shows selected frames from an intrinsic reaction coordinate scan from the transition state to the product for the oxidation of cis-1,2-dimethylcyclohexane.

    The potential-energy surfaces (PESs) of methyltrioxorhenium (MTO)-catalyzed CH insertion reactions in the presence of hydrogen peroxide were studied by accurate DFT methods for a series of substrates including unsaturated hydrocarbons, an ether, and an alcohol. Based on the comprehensive analysis of transition states and intrinsic reaction coordinate (IRC) scans, CH insertion was found to proceed by a concerted mechanism that does not require, as previously thought, a side-on or a butterfly-like transition state. We found that a typical transition state follows requirements of the SN2 reaction instead. Furthermore, by exploring the PESs of several CH insertion reactions, we discovered that no ionic intermediate is formed even in a polar solvent. The latter was modeled within the self-consistent reaction field approach in a polarizable continuum model (PB-SCRF/PCM). According to our study, CH insertion occurs by a concerted but highly asynchronous mechanism that first proceeds by hydride transfer and then turns into hydroxide transfer/rebound. For the oxidation of alcohols, CH bond cleavage occurs without formation of alkoxide intermediates on the dominant pathway. The computed deuterium kinetic isotope effect of 2.9 for the hydride-transfer transition state for alcohol oxidation is in good agreement with the experimental kH/kD ration of 3.2 reported by Zauche and Espenson. As confirmed by IRC and PES scans in different solvents, the OH-rebound phase of the CH insertion pathway demonstrates strong similarities with the rebound mechanism that was previously proposed for cytochrome P450 and metalloporphyrin-catalyzed oxidations.

  • 12.
    Kärkäs, Markus D.
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Johnston, Eric V.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Karlsson, Erik A.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Lee, Bao-Lin
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Åkermark, Torbjörn
    Shariatgorji, Mohammadreza
    Ilag, Leopold
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för analytisk kemi.
    Hansson, Örjan
    Bäckvall, Jan-E.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Åkermark, Björn
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Light-Induced Water Oxidation by a Ru-complex Containing a Bio-Inspired Ligand2011Inngår i: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 17, nr 28, s. 7953-7959Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The new Ru-complex 8 containing the bio-inspired ligand 7 was successfully synthesized and characterized. Complex 8 could efficiently catalyze water oxidation using CeIV and RuIII as chemical oxidants. More importantly, this complex has sufficiently low overpotential to utilize ruthenium polypyridyl-type complexes as photosensitizers.

  • 13.
    Laine, Tanja M.
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Kärkäs, Markus D.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Liao, Rong-Zhen
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi. Huazhong University of Science & Technology, People's Republic of China.
    Åkermark, Torbjörn
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Lee, Bao-Lin
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Karlsson, Erik A.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Siegbahn, Per E. M.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Åkermark, Björn
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Efficient photochemical water oxidation by a dinuclear molecular ruthenium complex2015Inngår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 51, nr 10, s. 1862-1865Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    Herein is described the preparation of a dinuclear molecular Ru catalyst for H2O oxidation. The prepared catalyst mediates the photochemical oxidation of H2O with an efficiency comparable to state-of-the-art catalysts.

  • 14. Nkambule, Comfort M.
    et al.
    Kwezi, Nomfundo W.
    Kinfe, Henok H.
    Nokwequ, Mbulelo G.
    Gammon, David W.
    Oscarson, Stefan
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Karlsson, Erik
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Efficient regioselective protection of myo-inositol via migration facile protecting group2011Inngår i: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 67, nr 3, s. 618-623Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    A cis-1,2-cyclohexanediol, 1,4,5,6-tetra-O-benzyl-myo-inositol, was selectively protected at the axial C2-hydroxyl via acid-mediated rearrangement of the corresponding 1,2-orthoacetate, or via the base-induced migration of a protecting group that had previously been easily installed with complete regioselectivity at the adjacent equatorial hydroxyl. Esters 4a-6a were synthesized in high yields (75-82%) while sulfonate 7a and silyl ether 8a were obtained in 85 and 31% yields, respectively. The migration of the esters induced by DBU results in equilibrium between regioisomers favouring the C2 protected isomer, but NaH induced migration of sulfonyl and silyl groups results in complete migration from equatorial to axial hydroxyl groups.

  • 15.
    Verho, Oscar
    et al.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Johnston, Eric
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Karlsson, Erik
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Bäckvall, Jan-E.
    Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
    Tuning of the Electronic Properties of a Cyclopentadienylruthenium Catalyst to Match Racemization of Electron-Rich and Electron-Deficient Alcohols2011Inngår i: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 17, nr 40, s. 11216-11222Artikkel i tidsskrift (Fagfellevurdert)
    Abstract [en]

    The synthesis of a new series of cyclopentadienylruthenium catalysts with varying electronic properties and their application in racemization of secondary alcohols are described. These racemizations involve two key steps: 1) β-hydride elimination (dehydrogenation) and 2) re-addition of the hydride to the intermediate ketone. The results obtained confirm our previous theory that the electronic properties of the substrate determine which of these two steps is rate determining. For an electron-deficient alcohol the rate-determining step is the β-hydride elimination (dehydrogenation), whereas for an electron-rich alcohol the re-addition of the hydride becomes the rate-determining step. By matching the electronic properties of the catalyst with the electronic properties of the alcohol, we have now shown that a dramatic increase in racemization rate can be obtained. For example, electron-deficient alcohol 15 racemized 30 times faster with electron-deficient catalyst 6 than with the unmodified standard catalyst 4. The application of these protocols will extend the scope of cyclopentadienylruthenium catalysts in racemization and dynamic kinetic resolution.

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