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  • 1.
    Bermejo Gómez, Antonio
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Holmberg, Pär
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martin-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Transition metal-catalyzed redox isomerization of codeine and morphine in water2014In: RSC Advances, ISSN 2046-2069, E-ISSN 2046-2069, Vol. 4, no 74, p. 39519-39522Article in journal (Refereed)
    Abstract [en]

    A water-soluble rhodium complex formed from commercially available [Rh(COD)(CH3CN)(2)]BF4 and 1,3,5-triaza-7-phosphaadamantane (PTA) catalyzes the isomerization of both codeine and morphine into hydrocodone and hydromorphone with very high efficiency. The reaction is performed in water, allowing isolation of the final products by simple filtration, which results in very high isolated yields. The reactions can be easily scaled up to 100 g.

  • 2.
    Carson, Fabian
    et al.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Martínez-Castro, Elisa
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Marcos, Rocio
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    González Miera, Greco
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Jansson, Kjell
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Zou, Xiaodong
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Martin-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Effect of the functionalisation route on a Zr-MOF with an Ir-NHC complex for catalysis2015In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 51, no 54, p. 10864-10867Article in journal (Refereed)
    Abstract [en]

    A new iridium N-heterocyclic carbene (NHC) metallolinker has been synthesised and introduced into a metal-organic framework (MOF), for the first time, via two different routes: direct synthesis and postsynthetic exchange (PSE). The two materials were compared in terms of the Ir loading and distribution using X-ray energy dispersive spectroscopy (EDS), the local Ir structure using X-ray absorption spectroscopy (XAS) and the catalytic activity. The materials showed good activity and recyclability as catalysts for the isomerisation of an allylic alcohol.

  • 3.
    Martinez-Erro, Samuel
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sanz-Marco, Amparo
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Gómez, Antonio Bermejo
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Vazquez-Romero, Ana
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ahlquist, Mårten S. G.
    Martin-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Base-Catalyzed Stereospecific Isomerization of Electron-Deficient Allylic Alcohols and Ethers through Ion-Pairing2016In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 138, no 40, p. 13408-13414Article in journal (Refereed)
    Abstract [en]

    A mild base-catalyzed strategy for the isomerization of allylic alcohols and allylic ethers has been developed. Experimental and computational investigations indicate that transition metal catalysts are not required when basic additives are present. As in the case of using transition metals under basic conditions, the isomerization catalyzed solely by base also follows a stereospecific pathway. The reaction is initiated by a rate-limiting deprotonation. Formation of an intimate ion pair between an allylic anion and the conjugate acid of the base results in efficient transfer of chirality. Through this mechanism, stereochemical information contained in the allylic alcohols is transferred to the ketone products. The stereospecific isomerization is also applicable for the first time to allylic ethers, yielding synthetically valuable enantioenriched (up to 97% ee) enol ethers.

  • 4.
    Pascanu, Vlad
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bermejo Gomez, Antonio
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ayats, Carles
    Platero-Prats, Ana Eva
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Carson, Fabian
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Su, Jie
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Yao, Qingxia
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Pericas, Miquel A.
    Zou, Xiaodong
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Martin-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Double-Supported Silica-Metal-Organic Framework Palladium Nanocatalyst for the Aerobic Oxidation of Alcohols under Batch and Continuous Flow Regimes2015In: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 5, no 2, p. 472-479Article in journal (Refereed)
    Abstract [en]

    Stable and easily synthesized metal-organic framework MIL-88B-NH2 represents an attractive support for catalysts employed in oxidation reactions, which are typically performed under relatively harsh conditions. However, MIL-88B-NH2, the thermodynamic polymorph of the more popular MIL-101-NH2, has been rarely employed in catalytic applications because of a difficult impregnation process caused by the flexible nature of the framework. We report herein a new catalyst denoted Pd@MIL-88B-NH2 (8 wt % Pd), the first example of metallic nanoparticles successfully impregnated in the pores of MIL-88B-NH2. Furthermore, by enclosing the MOF crystals in a tailored protective coating of SiO2 nanoparticles, an even more enduring material was developed and applied to the aerobic oxidation of benzylic alcohols. This doubly supported catalyst Pd@MIL-88B-NH2@nano-SiO2 displayed high activity and excellent performance in terms of endurance and leaching control. Under batch conditions, a very convenient and efficient recycling protocol is illustrated, using a teabag approach. Under continuous flow, the catalyst was capable of withstanding 7 days of continuous operation at 110 degrees C without deactivation. During this time, no leaching of metallic species was observed, and the material maintained its structural integrity.

  • 5.
    Platero-Prats, Ana E.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK). Argonne National Laboratory, USA.
    Bermejo Gómez, Antonio
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Chapman, Karena W.
    Martin-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zou, Xiaodong
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Functionalising metal-organic frameworks with metal complexes: the role of structural dynamics2015In: CrystEngComm, ISSN 1466-8033, E-ISSN 1466-8033, Vol. 17, no 40, p. 7632-7635Article in journal (Refereed)
    Abstract [en]

    A series of iridium-functionalised UiO-67 metal-organic frameworks (MOFs) were synthesised under conditions that simulate kinetically- and thermodynamically-controlled regimes. The degree of functionalisation depends on the reaction time and relative acidity of the native- and metallo-linkers, and can be optimised by controlling the reaction time.

  • 6.
    Platero-Prats, Ana E.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Bermejo Gómez, Antonio
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Samain, Louise
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Zou, Xiaodong
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Martin-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    The First One-Pot Synthesis of Metal-Organic Frameworks Functionalised with Two Transition-Metal Complexes2015In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 21, no 2, p. 861-866Article in journal (Refereed)
    Abstract [en]

    The synthesis of a metal-organic framework (UiO-67) functionalised simultaneously with two different transition metal complexes (Ir and Pd or Rh) through a one-pot procedure is reported for the first time. This has been achieved by an iterative modification of the synthesis parameters combined with characterisation of the resulting materials using different techniques, including X-ray absorption spectroscopy (XAS). The method also allows the first synthesis of UiO-67 with a very wide range of loadings (from 4 to 43 mol%) of an iridium complex ([IrCp*(bpydc)(Cl)Cl](2-); bpydc=2,2'-bipyridine-5,5'-dicarboxylate, Cp* = pentamethylcyclopentadienyl) through a pre-functionalisation methodology.

  • 7.
    Stewart, Beverly
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Nyhlén, Jonas
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martin-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Privalov, Timofei
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    A computational study of the CO dissociation in cyclopentadienyl ruthenium complexes relevant to the racemization of alcohols2013In: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, Vol. 42, no 4, p. 927-934Article in journal (Refereed)
    Abstract [en]

    The formation of an active 16-electron ruthenium sec-alkoxide complex via loss of the CO ligand is an important step in the mechanism of the racemization of sec-alcohols by (eta(5)-Ph5C5) Ru(CO)(2)X ruthenium complexes with X = Cl and OtBu. Here we show with accurate DFT calculations the potential energy profile of the CO dissociation pathway for a series of relevant (eta(5)-Ph5C5) Ru(CO) 2X complexes, where X = Cl, OtBu, H and (COOBu)-Bu-t. We have found that the CO dissociation energy increases in the following order: OtBu (lowest), Cl, COOtBu and H (highest). Using the distance between ruthenium and C-CO, r = Ru-C-CO, as a constraint, and by optimizing all other degrees of freedom for a range of Ru-CO distances, we obtained relative energies, Delta E(r) and geometries of a sufficient number of transient structures with the elongated Ru-CO bond up to r = 3.4 angstrom. Our calculations provide a quantitative understanding of the CO ligand dissociation in (eta(5)-Ph5C5) Ru(CO)(2)Cl and (eta(5)-Ph5C5) Ru(CO) 2(OtBu) complexes, which is relevant to the mechanism of their catalytic activity in the racemization of alcohols. We recently reported that exchange of the CO ligand by isotopically labeled (CO)-C-13 in the Ru-(OBu)-Bu-t complex occurs twenty times faster than that in the Ru-Cl complex. This corresponds to a difference of 1.8 kcal mol(-1) in the CO dissociation energy (at room temperature). This is in very good agreement with the calculated difference between the two potential energy curves for Ru-OtBu and Ru-Cl complexes, which is about 1.8-2 kcal mol(-1) around the corresponding transition states of the CO dissociation. The calculated difference in the total energy for CO dissociation in (eta(5)-Ph5C5) Ru(CO)(2)X complexes is related to the stabilization provided by the X group in the final 16-electron complexes, which are formed via product-like transition states. In addition to the calculated transition states of CO dissociation in Ru-OtBu and Ru-Cl complexes, the calculated transient structures with the elongated Ru-CO bond provide insight into how the geometry of the ruthenium complex with a potent heteroatom donor group (X) gradually changes when one of the COs is dissociating.

  • 8.
    Vazquez-Romero, Ana
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bermejo Gomez, Antonio
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martin-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Acid- and Iridium-Catalyzed Tandem 1,3-Transposition/3,1-Hydrogen Shift/Chlorination of Allylic Alcohols2015In: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 5, no 2, p. 708-714Article in journal (Refereed)
    Abstract [en]

    A method for the selective synthesis of alpha-chlorocarbonyls from allylic alcohols is presented. The reaction occurs through an acid- and iridium-catalyzed tandem process that combines a 1,3-transposition, a 3,1-hydrogen shift, and a chlorination process, and can be applied to a wide range of alpha-aromatic and heteroaromatic secondary allylic alcohols. Saturated non-chlorinated ketones or other side-products derived from overchlorination were not detected.

  • 9.
    Yao, Qingxia
    et al.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Bermejo Gómez, Antonio
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Su, Jie
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Pascanu, Vlad
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Yun, Yifeng
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Zheng, Haoquan
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Chen, Hong
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Liu, Leifeng
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Abdelhamid, Hani Nasser
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Martin-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zou, Xiaodong
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Series of Highly Stable Isoreticular Lanthanide Metal-Organic Frameworks with Expanding Pore Size and Tunable Luminescent Properties2015In: Chemistry of Materials, ISSN 0897-4756, E-ISSN 1520-5002, Vol. 27, no 15, p. 5332-5339Article in journal (Refereed)
    Abstract [en]

    A series of highly porous isoreticular lanthanide-based metal organic frameworks (LnMOFs) denoted as SUMOE-7I to SUMOE-7IV (SU = Stockholm University; Ln = La, Ce, Pr, Nd, Sm, Eu, and Gd) have been synthesized using tritopic carboxylates as the organic linkers. The SUMOF-7 materials display one-dimensional pseudohexagonal channels with the pore diameter gradually enlarged from 8.4 to 23.9 angstrom, as a result of increasing sizes of the organic linkers. The structures have been solved by single crystal X-ray diffraction or rotation electron diffraction (RED) combined with powder X-ray diffraction (PXRD). The SUMOF-7 materials exhibit robust architectures with permanent porosity. More importantly, they exhibit exceptionally high thermal and chemical stability. We show that, by inclusion of organic dye molecules, the luminescence properties of the MOFs can be elaborated and modulated, leading to promising applications in sensing and optics.

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