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  • 51.
    Angles d'Ortoli, Thibault
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of the tetrasaccharide glycoside moiety of Solaradixine and rapid NMR-based structure verification using the program CASPER2016In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 72, no 7, p. 912-927Article in journal (Refereed)
    Abstract [en]

    The major glycoalkaloid in the roots of Solanum laciniatum is Solaradixine having the branched tetrasaccharide beta-D-Glcp-(1 -> 2)-beta-D-Glcp-(1 -> 3)[alpha-L-Rhap-(1 -> 2)]-beta-D-Galp linked to O3 of the steroidal alkaloid Solasodine. We herein describe the synthesis of the methyl glycoside of the tetrasaccharide using a super-armed disaccharide as a donor molecule. A 2-(naphthyl)methyl protecting group was used in the synthesis of the donor since it was tolerant to a wide range of reaction conditions. The 6-O-benzylated-hexa-O-tert-butyldimethylsilyi-protected beta-D-Glcp-(1 -> 2)-beta-D-Glcp-SEt donor, which avoided 1,6-anydro formation, was successfully glycosylated at O3 of a galactoside acceptor molecule. However, subsequent glycosylation at O2 by a rhamnosyl donor was unsuccessful and instead a suitably protected alpha-L-Rhap(1 -> 2)-beta-D-Galp-OMe disaccharide was used as the acceptor molecule together with a super-armed beta-D-Glcp-(1 -> 2)-beta-D-Glcp-SEt donor in the glycosylation reaction, to give a tetrasaccharide in a yield of 55%, which after deprotection resulted in the target molecule, the structure of which was verified by the NMR chemical shift prediction program CASPER.

  • 52.
    Arafa, Wael A. A.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kärkäs, Markus D.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lee, Bao-Lin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Åkermark, Torbjörn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Liao, Rong-Zhen
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Berends, Hans-Martin
    Messinger, Johannes
    Siegbahn, Per E. M.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Åkermark, Björn
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Dinuclear manganese complexes for water oxidation: evaluation of electronic effects and catalytic activity2014In: Physical Chemistry, Chemical Physics - PCCP, ISSN 1463-9076, E-ISSN 1463-9084, Vol. 16, no 24, p. 11950-11964Article in journal (Refereed)
    Abstract [en]

    During recent years significant progress has been made towards the realization of a sustainable and carbon-neutral energy economy. One promising approach is photochemical splitting of H2O into O-2 and solar fuels, such as H-2. However, the bottleneck in such artificial photosynthetic schemes is the H2O oxidation half reaction where more efficient catalysts are required that lower the kinetic barrier for this process. In particular catalysts based on earth-abundant metals are highly attractive compared to catalysts comprised of noble metals. We have now synthesized a library of dinuclear Mn-2 (II,III) catalysts for H2O oxidation and studied how the incorporation of different substituents affected the electronics and catalytic efficiency. It was found that the incorporation of a distal carboxyl group into the ligand scaffold resulted in a catalyst with increased catalytic activity, most likely because of the fact that the distal group is able to promote proton-coupled electron transfer (PCET) from the high-valent Mn species, thus facilitating O-O bond formation.

  • 53. Arafa, Wael A. A.
    et al.
    Mohamed, Ashraf M.
    Abdel-Magied, Ahmed F.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    ULTRASOUND-MEDIATED THREE-COMPONENT REACTION ON-WATER PROTOCOL FOR THE SYNTHESIS OF NOVEL MONO- AND BIS-1,3-THIAZIN-4-ONE DERIVATIVES2017In: Heterocycles, ISSN 0385-5414, E-ISSN 1881-0942, Vol. 94, no 8, p. 1439-1455Article in journal (Refereed)
    Abstract [en]

    Green synthetic and catalyst-free strategy towards the synthesis of novel mono- and bis-1,3-thiazin-4-one scaffolds through a one pot, reaction of carbon disulfide, monoacetylenic esters and amines under ultrasonication has been reported. The merits of this protocol comprise no need for tedious workup steps and afforded the desired products in excellent yields make this synthetic protocol more efficient and worthy of further attentiveness. Moreover, the method exhibited excellent score in a number of green metrics.

  • 54. Arafa, Wael Abdelgayed Ahmed
    et al.
    Abdel-Magied, Ahmed Fawzy
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Nuclear Material Authority, Egypt.
    Utilization of ultrasonic irradiation as green and effective one-pot protocol to prepare a novel series of bis-2-amino-1,3,4-oxa(thia) diazoles and bis-tetrazoles2017In: ARKIVOC, ISSN 1551-7004, E-ISSN 1551-7012, p. 327-340Article in journal (Refereed)
    Abstract [en]

    In an effective and straightforward conversion, bis-semicarbazones and bis-thiosemicarbazones are transformed into a diversity of novel substituted bis-2-amino-1,3,4-oxadiazoles and bis-2-amino-1,3,4-thiadiazoles, respectively under ultrasonic irradiation. Bis-tetrazoles are obtained from the dialdehydes by sequential reaction with hydroxylamine hydrochloride, phosphorus pentoxide and sodium azide without isolation of the intermediates oximes and nitriles. All the reactions proceed cleanly and smoothly under mild conditions, with short reaction times and broad functional groups possibility. No side reactions were observed. [GRAPHICS]

  • 55. Arewång, Carl Johan
    et al.
    Lahmann, Martina
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Oscarson, Stefan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Tidén, Anna-Karin
    Synthesis of urine drug metabolites: glucuronic acid glycosides of phenol intermediates2007In: Carbohydrate Research, ISSN 0008-6215, Vol. 342, no 7, p. 970-974Article in journal (Refereed)
  • 56. Ashour, Radwa M.
    et al.
    Abdel-Magied, Ahmed F.
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Nuclear Materials Authority, Egypt.
    Abdel-Khalek, Ahmed A.
    Helaly, O. S.
    Ali, M. M.
    Preparation and characterization of magnetic iron oxide nanoparticles functionalized by L-cysteine: Adsorption and desorption behavior for rare earth metal ions2016In: Journal of Environmental Chemical Engineering, ISSN 2160-6544, E-ISSN 2213-3437, Vol. 4, no 3, p. 3114-3121Article in journal (Refereed)
    Abstract [en]

    In this work, magnetic iron oxide nanoparticles functionalized with L-cysteine (Cys-Fe3O4 NPs) was synthesized and fully characterized by transmission electron microscopy (TEM), X-ray powder diffraction (XRD), Fourier transform infra-red (FTIR), thermogravimetric analysis (TGA) and zeta potential measurements. The synthesized Cys-Fe(3)O(4)NPs has been evaluated as a highly adsorbent for the adsorption of a mixture of four rare earths RE3+ ions (La3+, Nd3+, Gd3+ and Y3+) from digested monazite solutions. The influence of various factors on the adsorption efficiency such as, the contact time, sample pH, temperature, and concentration of the stripping solution were investigated. The results indicate that Cys-Fe3O4 NPs achieve high removal efficiency 96.7, 99.3, 96.5 and 87% for La3+, Nd3+, Gd3+ and Y3+ ions, respectively, at pH = 6 within 15 min, and the adsorbent affinity for metal ions was found to be in order of Nd3+ > La3+ > Gd3+ > Y3+ ions. Using the Langmuir model, a maximum adsorption capacity of La3+, Nd3+, Gd3+ and Y3+ at room temperature was found to be 71.5, 145.5, 64.5 and 13.6 mg g (1), respectively. The Langmuir isotherm and pseudo-second order model fitted much better than the other isotherms and kinetic models. The obtained results for the thermodynamic parameters confirmed the spontaneous and endothermic nature of the process. Moreover, the desorption was carried out with 0.1 M nitric acid solutions. In addition, Cys-Fe3O4 NPs can be used as a highly efficient adsorbent for the adsorption of La3+, Nd3+, Gd3+ and Y3+ ions from digested monazite solutions.

  • 57.
    Aydin, Juhanes
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Conrad, Cathrin S.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Stereoselective pincer-complex catalyzed C-H functionalization of benzyl nitriles under mild conditions. An efficient route to β-aminonitriles2008In: Organic Letters, ISSN 1523-7060, Vol. 10, no 22, p. 5175-5178Article in journal (Refereed)
  • 58.
    Aydin, Juhanes
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kumar, K. Senthil
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry.
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium pincer complex-catalyzed condensation of sulfonimines and isocyanoacetate to imidazoline derivatives. Dependence of the stereoselectivity on the ligand effects2007In: Advanced Synthesis & Catalysis, ISSN 1615-4150, Vol. 349, no 17-18, p. 2585-2594Article in journal (Refereed)
  • 59.
    Aydin, Juhanes
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kumar, K. Senthil
    Sayah, Mahmoud J.
    Wallner, Olov A.
    Szabó, Kálmán J.
    Synthesis and Catalytic Application of Chiral 1,1‘-Bi-2-naphthol- and Biphenanthrol-Based Pincer Complexes: Selective Allylation of Sulfonimines with Allyl Stannane and Allyl Trifluoroborate2007In: The Journal of Organic Chemistry, ISSN 0022-3263, Vol. 72, no 13, p. 4689-4697Article in journal (Refereed)
  • 60.
    Aydin, Juhanes
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Larsson, Johanna M.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Selander, Nicklas
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Pincer complex-catalyzed redox coupling of alkenes with iodonium salts via presumed palladium(IV) intermediates2009In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 11, no 13, p. 2852-2854Article in journal (Refereed)
    Abstract [en]

    Palladium pincer complexes directly catalyze the redox coupling reactions of functionalized alkenes and iodonium salts. The catalytic process, which is suitable for mild catalytic functionalization of allylic acetates and electron-rich alkenes, probably occurs through Pd(IV) intermediates. Due to the strong metal−ligand interactions, the oxidation of phosphine and amine ligands of the pincer complexes can be avoided in the presented reactions.

  • 61.
    Aydin, Juhanes
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Larsson, Johanna M.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Pincer Complex-Catalyzed Coupling Reactions via Palladium (IV) Intermediates2009In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 11, no 13, p. 2852-2854Article in journal (Refereed)
    Abstract [en]

    Palladium pincer complexes directly catalyze the redox coupling reactions of functionalized alkenes and iodonium salts. The catalytic process, which is suitable for mild catalytic functionalization of allylic acetates and electron-rich alkenes, probably occurs through Pd(IV) intermediates. Due to the strong metal−ligand interactions, the oxidation of phosphine and amine ligands of the pincer complexes can be avoided in the presented reactions.

  • 62.
    Aydin, Juhanes
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rydén, Andreas
    Szabó, Kálmán J.
    Chiral palladium-pincer complex catalyzed asymmetric condensation of sulfonimines and isocyanoacetate2008In: Tetrahedron: Asymmetry, ISSN 0957-4166, Vol. 19, no 15, p. 1867-1870Article in journal (Refereed)
  • 63.
    Aydin, Juhanes
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Selander, Nicklas
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán J.
    Strategies for fine-tuning the catalytic activity of pincer-complexes2006In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 47, no 50, p. 8999-9001Article in journal (Refereed)
    Abstract [en]

    Various methoxy substituted pincer-complexes were prepared in order to study the substituent effects on the catalytic activity in palladium catalyzed opening of vinyl epoxides and boronation of cinnamyl alcohol. The results clearly show that methoxy substitution at the para-position of the pincer-complex leads to up to fourfold acceleration of the catalytic reactions, while substitution of the side-arms does not change the activity of the complex or leads to a slight deceleration of the catalytic processes.

  • 64.
    Aydin, Juhanes
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Senthil, Kumar K
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sayah, Mahmoud J
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Wallner, Olov A
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán J
    Synthesis and catalytic application of chiral 1,1'-Bi-2-naphthol- and biphenanthrol-based pincer complexes: selective allylation of sulfonimines with allyl stannane and allyl trifluoroborate.2007In: Journal of Organic Chemistry, Vol. 72, no 13, p. 4689-4697Article in journal (Refereed)
    Abstract [en]

    New easily accessible 1,1'-bi-2-naphthol- (BINOL-) and biphenanthrol-based chiral pincer complex catalysts were prepared for selective (up to 85% enantiomeric excess) allylation of sulfonimines. The chiral pincer complexes were prepared by a flexible modular approach allowing an efficient tuning of the selectivity of the catalysts. By employment of the different enantiomeric forms of the catalysts, both enantiomers of the homoallylic amines could be selectively obtained. Both allyl stannanes and allyl trifluoroborates can be employed as allyl sources in the reactions. The biphenanthrol-based complexes gave higher selectivity than the substituted BINOL-based analogues, probably because of the well-shaped chiral pocket generated by employment of the biphenanthrol complexes. The enantioselective allylation of sulfonimines presented in this study has important implications for the mechanism given for the pincer complex-catalyzed allylation reactions, confirming that this process takes place without involvement of palladium(0) species.

  • 65.
    Aydin, Juhanes
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium-pincer complex catalyzed C-C coupling of allyl nitriles with tosyl imines via regioselective allylic C-H bond functionalization2008In: Organic Letters, ISSN 1523-7060, Vol. 10, no 13, p. 2881-2884Article in journal (Refereed)
    Abstract [en]

    A mechanistically new palladium-pincer complex catalyzed allylation of sulfonimines is presented. This reaction involves C-H bond functionalization of allyl nitriles under mild conditions. The reaction proceeds with a high regioselectivity, without allyl rearrangement of the product. Modeling studies indicate that the carbon-carbon bond formation process proceeds via (η1-allyl)palladium pincer complex intermediates.

  • 66.
    Ayesa, Susana
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Argyopoulus, Dimitris
    Maltseva, Tatiana
    Sund, Christian
    Samuelsson, Bertil
    An Expeditious Library Synthesis of N-Monoalkylated Aminopiperidines and –pyrrolidines2004In: European Journal of Organic Chemistry, ISSN 1434-193x, no 12, p. 2723-2737Article in journal (Refereed)
  • 67.
    Ayesa, Susana
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Chen, Jing-May
    Classon, Björn
    Gallego, Jose
    Grabowska, Urszula
    Henderson, Ian
    Heyer, Narinder
    Johnson, Tony
    Kangasmetsä, Jussi
    Liley, Mark
    Nilsson, Magnus
    Parkes, Kevin
    Rakos, Laszlo
    Tozer, Matthew J.
    Wilson, Michelle
    Preparation and Characterization of Aminoethylamide Inhibitors of the Cysteine Proteinase Cathepsin KIn: European Journal of Medicinal Chemistry, ISSN 0223-5234Article in journal (Refereed)
  • 68.
    Ayesa, Susana
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lindquist, Charlotta
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Agback, Tatiana
    Benkestock, Kurt
    Classon, Björn
    Henderson, Ian
    Hewitt, Ellen
    Jansson, Katarina
    Kallin, Anders
    Sheppard, Dave
    Samuelsson, Bertil
    Solid-phase parallel synthesis and SAR of 4-amidofuran-3-one inhibitors of cathepsin S: Effect of sulfonamides P3 substituents on potency and selectivity.2009In: Bioorganic & Medicinal Chemistry, ISSN 0968-0896, E-ISSN 1464-3391, Vol. 17, no 3, p. 1307-1324Article in journal (Refereed)
    Abstract [en]

    Highly potent and selective 4-amidofuran-3-one inhibitors of cathepsin S are described. The synthesis and structure–activity relationship of a series of inhibitors with a sulfonamide moiety in the P3 position is presented. Several members of the series show sub-nanomolar inhibition of the target enzyme as well as an excellent selectivity profile and good cellular potency. Molecular modeling of the most interesting inhibitors describes interactions in the extended S3 pocket and explains the observed selectivity towards cathepsin K.

  • 69.
    Ayesa, Susana
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Samuelsson, Bertil
    Classon, Björn
    A One-Pot, Solid-Phase Synthesis of Secondary Amines from Reactive Alkyl Halides and an Alkyl Azide2008In: Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, ISSN 0936-5214, E-ISSN 1437-2096, no 1, p. 77-79Article in journal (Refereed)
  • 70.
    Babu, Beneesh P.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Endo, Yoshinori
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Biomimetic Aerobic Oxidation of Amino Alcohols to Lactams2012In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 18, no 37, p. 11524-11527Article in journal (Refereed)
  • 71.
    Babu, Beneesh P.
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Meng, Xu
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Aerobic Oxidative Coupling of Arenes and Olefins through a Biomimetic Approach2013In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 19, no 13, p. 4140-4145Article in journal (Refereed)
  • 72. Back, Marcus
    et al.
    Nyhlen, Jonas
    Kvarnstrom, Ingemar
    Appelgren, Sara
    Borkakoti, Neera
    Jansson, Katarina
    Lindberg, Jimmy
    Nystrom, Susanne
    Hallberg, Anders
    Rosenquist, Asa
    Samuelsson, Bertil
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Design, synthesis and SAR of potent statine-based BACE-1 inhibitors: Exploration of P1 phenoxy and benzyloxy residues2008In: Bioorganic & Medicinal Chemistry, ISSN 0968-0896, E-ISSN 1464-3391, Vol. 16, no 21, p. 9471-9486Article in journal (Refereed)
    Abstract [en]

    Several BACE-1 inhibitors with low nanomolar level activities, encompassing a statine-based core structure with phenyloxymethyl- and benzyloxymethyl residues in the P1 position, are presented. The novel P1 modi. cation introduced to allow the facile exploration of the S1 binding pocket of BACE-1, delivered highly promising inhibitors.

  • 73.
    Bacsik, Zoltan
    et al.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Ahlsten, Nanna
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ziadi, Asraa
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Guoying
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Garcia-Bennett, Alfonso E.
    Uppsala universitet.
    Martin-Matute, Belen
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Hedin, Niklas
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Mechanisms and Kinetics for Sorption of CO(2) on Bicontinuous Mesoporous Silica Modified with n-Propylamine2011In: Langmuir, ISSN 0743-7463, E-ISSN 1520-5827, Vol. 27, no 17, p. 11118-11128Article in journal (Refereed)
    Abstract [en]

    We studied equilibrium adsorption and uptake kinetics and identified molecular species that formed during sorption of carbon dioxide on amine-modified silica. Bicontinuous silicas (AMS-6 and MCM-48) were postsynthetically modified with (3-aminopropyl)triethoxysilane or (3-aminopropyl)methyldiethoxysilane, and amine-modified AMS-6 adsorbed more CO(2) than did amine-modified MCM-48. By in situ FTIR spectroscopy, we showed that the amine groups reacted with CO(2) and formed ammonium carbamate ion pairs as well as carbamic acids under both dry and moist conditions. The carbamic acid was stabilized by hydrogen bonds, and ammonium carbamate ion pairs formed preferably on sorbents with high densities of amine groups. Under dry conditions, silylpropylcarbamate formed, slowly, by condensing carbamic acid and silanol groups. The ratio of ammonium carbamate ion pairs to silylpropylcarbamate was higher for samples with high amine contents than samples with low amine contents. Bicarbonates or carbonates did not form under dry or moist conditions. The uptake of CO(2) was enhanced in the presence of water, which was rationalized by the observed release of additional amine groups under these conditions and related formation of ammonium carbamate ion pairs. Distinct evidence for a fourth and irreversibly formed moiety was observed under sorption of CO(2) under dry conditions. Significant amounts of physisorbed, linear CO(2) were detected at relatively high partial pressures of CO(2), such that they could adsorb only after the reactive amine groups were consumed.

  • 74.
    Balan, Daniela
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Adolfsson, Hans
    Chiral quinuclidine-based amine catalysts for the asymmetric one-pot, three-component aza-Baylis–Hillman reaction2003In: Tetrahedron Letters, Vol. 44, no 12, p. 2521-2524Article in journal (Refereed)
  • 75.
    Balan, Daniela
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Adolfsson, Hans
    Efficient microwave-assisted formation of functionalized 2,5-dihydropyrroles using ruthenium-catalyzed ring-closing metathesis2004In: Tetrahedron Letters, Vol. 45, no 15, p. 3089-3092Article in journal (Refereed)
  • 76.
    Balan, Daniela
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Adolfsson, Hans
    Selective formation of α-methylene-β-amino acid derivatives through the aza version of the baylis-Hillman reaction2001In: The Journal of Organic Chemistry, Vol. 66, p. 6498-6501Article in journal (Refereed)
  • 77.
    Balan, Daniela
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Adolfsson, Hans
    Titanium isopropoxide as Efficient Catalyst for the aza-Baylis-Hillman reaction. Selective formation of α-methylene-β-amino acid derivatives2002In: The Journal of Organic Chemistry, Vol. 67, p. 2329-2334Article in journal (Refereed)
  • 78. Barbion, Julien
    et al.
    Sorin, Geoffroy
    Selkti, Mohamed
    Kellenberger, Esther
    Baati, Rachid
    Santoro, Stefano
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Himo, Fahmi
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Pancrazi, Ange
    Lannou, Marie-Isabelle
    Ardisson, Janick
    Stereoselective functionalization of pyrrolidinone moiety towards the synthesis of salinosporamide A2012In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 68, no 32, p. 6504-6512Article in journal (Refereed)
    Abstract [en]

    An important feature of the synthesis of salinosporamide A. a potent proteasome inhibitor, is the establishment of the quaternary stereocenter at C3. A new route has been developed based on the methylation of a functionalized pyrrolidinone. Direct methylation reaction led to the unwanted diastereomer: however, by means of a Corey-Chaykovsky reaction followed by LiAlH4 epoxide opening, the desired alcohol was obtained. The pyrrolidinone was elaborated through a key allylation reaction between a tertiary allyltitanium reagent and an aldehyde bearing a spiroketal moiety in alpha-position.

  • 79.
    Bartholomeyzik, Teresa
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Mazuela, Javier
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Pendrill, Robert
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Deng, Youqian
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium-Catalyzed Oxidative Arylating Carbocyclization of Allenynes: Control of Selectivity and Role of H2O2014In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 53, no 33, p. 8696-8699Article in journal (Refereed)
    Abstract [en]

    Highly selective protocols for the carbocyclization/arylation of allenynes using arylboronic acids are reported. Arylated vinylallenes are obtained with the use of BF3 center dot Et2O as an additive, whereas addition of water leads to arylated trienes. These conditions provide the respective products with excellent selectivities (generally > 97:3) for a range of boronic acids and different allenynes. It has been revealed that water plays a crucial role for the product distribution.

  • 80.
    Bartholomeyzik, Teresa
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Pendrill, Robert
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lihammar, Richard
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Jiang, Tuo
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kinetics and Mechanism of the Palladium-Catalyzed Oxidative Arylating Carbocyclization of Allenynes2018In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 140, no 1, p. 298-309Article in journal (Refereed)
    Abstract [en]

    Pd-catalyzed C-C bond-forming reactions under oxidative conditions constitute a class of important and widely used synthetic protocols. This Article describes a mechanistic investigation of the arylating carbocyclization of allenynes using boronic acids and focuses on the correlation between reaction conditions and product selectivity. Isotope effects confirm that either allenic or propargylic C-H activation occurs directly after substrate binding. With an excess of H2O, a triene product is selectively formed via allenic C-H activation. The latter C-H activation was found to be turnover-limiting and the reaction zeroth order in reactants as well as the oxidant. A dominant feature is continuous catalyst activation, which was shown to occur even in the absence of substrate. Smaller amounts of H2O lead to mixtures of triene and vinylallene products, where the latter is formed via propargylic C-H activation. The formation of triene occurs only in the presence of ArB(OH)(2). Vinylallene, on the other hand, was shown to be formed by consumption of (ArBO)(3) as a first-order reactant. Conditions with sub-stoichiometric BF3 center dot OEt2 gave selectively the vinylallene product, and the reaction is first order in PhB(OH)(2). Both C-H activation and transmetalation influence the reaction rate. However, with electron-deficient ArB(OH)(2), C-H activation is turnover-limiting. It was difficult to establish the order of transmetalation vs C-H activation with certainty, but the results suggest that BF3 center dot OEt2 promotes an early transmetalation. The catalytically active species were found to be dependent on the reaction conditions, and H2O is a crucial parameter in the control of selectivity.

  • 81.
    Bartoszewicz, Agnieszka
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    González Miera, Greco
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Marcos, Rocio
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Norrby, Per-Ola
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Mechanistic Studies on the Alkylation of Amines with Alcohols Catalyzed by a Bifunctional Iridium Complex2015In: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 5, no 6, p. 3704-3716Article in journal (Refereed)
    Abstract [en]

    The mechanism of the N-alkylation of amines with alcohols catalyzed by an iridium complex containing an N-heterocyclic carbene (NHC) ligand with a tethered alcohol/alkoxide functionality was investigated by a combination of experimental and computational methods. The catalyst resting state is an iridium hydride species containing the amine substrate as a ligand, and decoordination of the amine, followed by coordination of the imine intermediate to the iridium center, constitute the rate-determining step (rds) of the catalytic process. The alcohol/alkoxide that is tethered to the NHC participates in every step of the catalytic cycle by accepting or releasing protons and forming hydrogen bonds with the reacting species. Thus, the iridium complex with the alcohol/alkoxide tethered to the N-heterocyclic carbene ligand acts as a bifunctional catalyst.

  • 82.
    Bartoszewicz, Agnieszka
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Jezowska, Martina M.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Laymand, Kevin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Mobus, Juri
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of β-Hydroxy and β-Amino Ketones from Allylic Alcohols Catalyzed by Ru(η5-C5Ph5)(CO)2Cl2012In: European Journal of Inorganic Chemistry, ISSN 1434-1948, E-ISSN 1099-1948, no 9, p. 1517-1530Article in journal (Refereed)
    Abstract [en]

    An efficient method for the synthesis of beta-hydroxy and beta-amino ketones from allylic alcohols catalyzed by Ru(5-C5Ph5)(CO)2Cl is described. The influence of the stereoelectronic properties of the catalyst on the reaction outcome has been studied. Optimization of the reaction conditions supressed the formation of undesired side products such as saturated ketones, benzyl alcohols, and a,beta-unsaturated ketones. Several aromatic and aliphatic allylic alcohols have been reacted with a large variety of aldehydes or imines to produce beta-hydroxy ketones or beta-amino ketones, respectively, in yields up to 99%. Based on experimental data, a mechanism via ruthenium alkoxides and ruthenium aldoxides is proposed. In addition, a C-bound ruthenium enolate has been characterized.

  • 83.
    Bartoszewicz, Agnieszka
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kalek, Marcin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Stawinski, Jacek
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Iodine-promoted silylation of alcohols with silyl chlorides. Synthetic and mechanistic studies2008In: Tetrahedron, ISSN 0040-4020, Vol. 64, no 37, p. 8843-8850Article in journal (Refereed)
  • 84.
    Bartoszewicz, Agnieszka
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kalek, Marcin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Stawinski, Jacek
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    The case for the intermediacy of monomeric metaphosphate analogues during oxidation of H-phosphonothioate, H-phosphonodithioate, and H-phosphonoselenoate monoesters: mechanistic and synthetic studies2008In: The Journal of Organic Chemistry, ISSN 0022-3263, Vol. 73, no 13, p. 5029-5038Article in journal (Refereed)
  • 85.
    Bartoszewicz, Agnieszka
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Livendahl, Madeleine
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Efficient synthesis of beta-hydroxy ketones from allylic alcohols by catalytic formation of ruthenium enolates2008In: Chemistry: a European Journal, ISSN 0947-6539, Vol. 14, no 34, p. 10547-10550Article in journal (Refereed)
  • 86.
    Bartoszewicz, Agnieszka
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Livendahl, Madeleine
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of b-Hydroxy Ketones from Allylic Alcohols via Catalytic Formation of Ruthenium Enolates2008In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 14, no 34, p. 10547-10550Article in journal (Refereed)
    Abstract [en]

    The most efficient Ru-catalyzed isomerization–aldol reaction from allylic alcohols has been achieved by using [η5-(Ph5Cp)Ru(CO)2Cl] as the catalyst. The bulky pentaphenylcyclopentadienyl ligand on the ruthenium atom prevents protonation at the oxygen of the Ru–enolate intermediate and completely suppresses the formation of unwanted ketone byproducts (see scheme). The domino transformation is as good as it can be: aldols are obtained in quantitative yields at ambient temperature.

  • 87.
    Bartoszewicz, Agnieszka
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Building molecular complexity via tandem Ru-catalyzed isomerization/C-H activation2009In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 11, no 8, p. 1749-1752Article in journal (Refereed)
    Abstract [en]

    A tandem isomerization/C-H activation of allylic alcohols was performed using a catalytic amount of RUCl(2)(PPh(3))(3). A variety of ortho alkylated ketones have been obtained in excellent yields. This tandem process relies on an in situ generation of a carbonyl functional group that directs the ortho C-H bond activation.

  • 88. Battistel, Marcos D.
    et al.
    Pendrill, Robert
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Freedberg, Daron I.
    Direct Evidence for Hydrogen Bonding in Glycans: A Combined NMR and Molecular Dynamics Study2013In: Journal of Physical Chemistry B, ISSN 1520-6106, E-ISSN 1520-5207, Vol. 117, no 17, p. 4860-4869Article in journal (Refereed)
    Abstract [en]

    We introduce the abundant hydroxyl groups of glycans as NMR handle's and structural probes to expand the repertoire of tools for structure function studies on glycans in solution. To this end, we present the facile detection and assignment of hydroxyl groups in a Wide range of sample concentrations (0.5-1700 mM) and temperatures, ranging from -5 to 25 degrees C.,We then exploit this information to directly detect hydrogen bonds, well-known for their importance in molecular structural determination through NMR. Via HSQC-TOCSY, we were able to determine the directionality; of these hydrogen bonds in sucrose Furthermore, by means Of molecular dynamics simulations in conjunction with NMR, we establish that one Out of the three detected hydrogen bonds arises from intermolecular interactions. This finding may shed light on glycan glycan interactions and glycan recognition by proteins.

  • 89. Bejhed, Rebecca S.
    et al.
    Tian, Bo
    Eriksson, Kristofer
    Brucas, Rimantas
    Oscarsson, Sven
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Strömberg, Mattias
    Svedlindh, Peter
    Gunnarsson, Klas
    Magnetophoretic Transport Line System for Rapid On-Chip Attomole Protein Detection2015In: Langmuir, ISSN 0743-7463, E-ISSN 1520-5827, Vol. 31, no 37, p. 10296-10302Article in journal (Refereed)
    Abstract [en]

    A lab-on-a-chip traveling wave magnetophoresis approach for sensitive and rapid protein detection is reported. In this method, a chip-based magnetic microarray comprising lines of micrometer-sized thin film magnetic elements was used to control the movement of magnetic beads (MBs). The MBs and the chip were functionalized, forming a sandwich-type assay. The MBs were transported across a detection area, and the presence of target molecules resulted in the immobilization of MBs within this area. Target quantification was accomplished by MB counting in the detection area using an optical microscope. In order to demonstrate the versatility of the microarray, biotinylated antiavidin was selected as the target protein. In this case, avidin-functionalized MBs and an avidin-functionalized detection area were used. With a total assay time of 1 to 1.5 h (depending on the labeling approach used), a limit of detection in the attomole range was achieved. Compared to on-chip surface plasmon resonance biodetection systems, our method has a larger dynamic range and is about a factor of 500 times more sensitive. Furthermore, our MB transportation system can operate in any chip-based biosensor platform, thereby significantly improving traditional biosensors.

  • 90.
    Belhomme, Marie-Charlotte
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Wang, Dong
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Formation of C(sp(3))-C(sp(3)) Bonds by Palladium Catalyzed Cross-Coupling of alpha-Diazoketones and Allylboronic Acids2016In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 18, no 10, p. 2503-2506Article in journal (Refereed)
    Abstract [en]

    Palladium catalyzed cross-coupling of allylboronic acids with a-diazoketones was studied. The reaction selectively affords the linear allylic product. The reaction proceeds with formation of a new C(sp(3))-C(sp(3)) bond. The reaction was performed without an external oxidant, likely without the Pd-catalyst undergoing redox reactions.

  • 91. Bergenstråhle-Wohlert, Malin
    et al.
    Angles d'Ortoli, Thibault
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sjöberg, Nils A.
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Wohlert, Jakob
    On the anomalous temperature dependence of cellulose aqueous solubility2016In: Cellulose (London), ISSN 0969-0239, E-ISSN 1572-882X, Vol. 23, no 4, p. 2375-2387Article in journal (Refereed)
    Abstract [en]

    The solubility of cellulose in water-based media is promoted by low temperature, which may appear counter-intuitive. An explanation to this phenomenon has been proposed that is based on a temperature-dependent orientation of the hydroxymethyl group. In this paper, this hypothesis is investigated using molecular dynamics computer simulations and NMR spectroscopy, and is discussed in conjunction with alternative explanations based on solvent–solute and solvent–solvent hydrogen bond formation respectively. It is shown that neither simulations nor experiments lend support to the proposed mechanism based on the hydroxymethyl orientation, whereas the two alternative explanations give rise to two distinct contributions to the hydration free energy of cellooligomers.

  • 92. Berggren, Gustav
    et al.
    Kaynak, Filiz Betul
    Anderlund, Magnus F.
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry.
    Åkermark, Björn
    Department of Organic Chemistry.
    Tetraethylammonium [12,12-diethyl-2,2,9,9-tetramethyl-1,4,7,10-tetraza-5,6-benzotridecane-3,8,11,13-tetra-one(4-)]oxidomanganate(V)2007In: Acta Crystallographica Section E, ISSN 1600-5368, Vol. E63, p. m2672-m2673Article in journal (Refereed)
  • 93. Berglund, Jennie
    et al.
    Angles d'Ortoli, Thibault
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Vilaplana, Francisco
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bergenstråhle-Wohlert, Malin
    Lawoko, Martin
    Henriksson, Gunnar
    Lindström, Mikael
    Wohlert, Jakob
    A molecular dynamics study of the effect of glycosidic linkage type in the hemicellulose backbone on the molecular chain flexibility2016In: The Plant Journal, ISSN 0960-7412, E-ISSN 1365-313X, Vol. 88, no 1, p. 56-70Article in journal (Refereed)
    Abstract [en]

    The macromolecular conformation of the constituent polysaccharides in lignocellulosic biomass influences their supramolecular interactions, and therefore their function in plants and their performance in technical products. The flexibility of glycosidic linkages from the backbone of hemicelluloses was studied by evaluating the conformational freedom of the φ and ψ dihedral angles using molecular dynamic simulations, additionally selected molecules were correlated with experimental data by NMR spectroscopy. Three types of β-(1→4) glycosidic linkages involving the monosaccharides (Glcp, Xylp and Manp) present in the backbone of hemicelluloses were defined. Different di- and tetrasaccharides with combinations of such sugar monomers from hemicelluloses were simulated and free energy maps of the φ - ψ space and hydrogen bonding patterns were obtained. The glycosidic linkage between Glc-Glc or Glc-Man (C-type) was the stiffest with mainly one probable conformation; the linkage from Man-Man or Man-Glc (M-type) was similar but with an increased probability for an alternative conformation making it more flexible, and the linkage between two Xyl-units (X-type) was the most flexible with two almost equally populated conformations. Glycosidic linkages of the same type showed essentially the same conformational space in both disaccharides and in the central region of tetrasaccharides. Different probabilities of glycosidic linkage conformations in the backbone of hemicelluloses can be directly estimated from the free energy maps, which to a large degree affect the overall macromolecular conformations of these polymers. The information gained contributes to an increased understanding of hemicelluloses’ function both in the cell wall and in technical products.

  • 94.
    Bermejo Gomez, Antonio
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Erbing, Elis
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Batuecas, Maria
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Vazquez-Romero, Ana
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martin-Matute, Belen
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Iridium-Catalyzed Isomerization/Bromination of Allylic Alcohols: Synthesis of alpha-Bromocarbonyl Compounds2014In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 20, no 34, p. 10703-10709Article in journal (Refereed)
    Abstract [en]

    alpha-Brominated ketones and aldehydes, with two adjacent electrophilic carbon atoms, are highly valuable synthetic intermediates in organic synthesis, however, their synthesis from unsymmetrical ketones is very challenging, and current methods suffer from low selectivity. We present a new, reliable, and efficient method for the synthesis of alpha-bromocarbonyl compounds in excellent yields and with excellent selectivities. Starting from allylic alcohols as the carbonyl precursors, the combination of a 1,3-hydrogen shift catalyzed by iridium(III) with an electrophilic bromination gives alpha-bromoketones and aldehydes in good to excellent yields. The selectivity of the process is determined by the structure of the starting allylic alcohol; thus, alpha-bromoketones formally derived from unsymmetrical ketones can be synthesized in a straightforward and selective manner.

  • 95. Bermejo Góme, Antonio
    et al.
    Cortés González, Miguel A.
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Karolinska Intitutet, Sweden.
    Lübcke, Marvin
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Karolinska Intitutet, Sweden.
    Johansson, Magnus J.
    Schou, Magnus
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Karolinska Intitutet, Sweden.
    Synthesis of trifluoromethyl moieties by late-stage copper (I) mediated nucleophilic fluorination2017In: Journal of fluorine chemistry, ISSN 0022-1139, E-ISSN 1873-3328, Vol. 194, p. 51-57Article in journal (Refereed)
    Abstract [en]

    The nucleophilic fluorination of bromodifluoromethyl derivatives mediated by the complex (PPh3)(3)CuF is described. Under the reaction conditions, different trifluoroacetates, trifluorolcetones, trifluoroarenes and trifluoroacetamides were obtained in good yields.

  • 96.
    Bermejo Gómez, Antonio
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ahlsten, Nanna
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Platero-Prats, Ana E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of 4,5-disubstituted 2-aminothiazoles from a,b-unsaturated ketones: Preparation of 5-benzyl-4-methyl-2-aminothiazolium hydrochloride salt2014In: Organic Syntheses, ISSN 0078-6209, Vol. 91, p. 185-200Article in journal (Refereed)
  • 97.
    Bermejo Gómez, Antonio
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Karolinska Universitetssjukhuset, Sweden; Karolinska Institutet, Sweden.
    Cortés González, Miguel A.
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Karolinska Institutet, Sweden.
    Lübcke, Marvin
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Karolinska Institutet, Sweden.
    Johansson, Magnus J.
    Halldin, Christer
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Karolinska Insitutet, Sweden.
    Schou, Magnus
    Efficient DBU accelerated synthesis of F-18-labelled trifluoroacetamides2016In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 52, no 97, p. 13963-13966Article in journal (Refereed)
    Abstract [en]

    Nucleophilic F-18-fluorination of bromodifluoromethyl derivatives was performed using [F-18] Bu4NF in the presence of DBU(1,8-diazabicyclo[5.4.0]undec-7-ene). This novel procedure provided a diverse set of [F-18] trifluoroacetamides in good to excellent radiochemical conversions. A mechanism where DBU acts as organomediator in this transformation is proposed.

  • 98.
    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.

  • 99. Berner, Simon
    et al.
    Lidbaum, Hans
    Ledung, Greger
    Åhlund, John
    Nilson, Katharina
    Schiessling, Joachim
    Gelius, Ulrik
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Puglia, Carla
    Oscarsson, Sven
    Electronic and structural studies of immobilized thiol-derivatized cobalt porphyrins on gold surfaces2007In: Applied Surface Science, ISSN 0169-4332, Vol. 253, no 18, p. 7540-7548Article in journal (Refereed)
  • 100. Betterley, Nolan M.
    et al.
    Kerdphon, Sutthichat
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Chaturonrutsamee, Suppisak
    Kongsriprapan, Sopanat
    Surawatanawong, Panida
    Soorukram, Darunee
    Pohmakotr, Manat
    Andersson, Pher G.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Reutrakul, Vichai
    Kuhakarn, Chutima
    Bi(OTf)(3) Enabled C-F Bond Cleavage in HFIP: Electrophilic Aromatic Formylation with Difluoro(phenylsulfanyl)methane2018In: Asian Journal of Organic Chemistry, ISSN 2193-5807, Vol. 7, no 8, p. 1642-1647Article in journal (Refereed)
    Abstract [en]

    Bismuth(III) trifluoromethanesulfonate [Bi(OTf)(3)] mediated mild electrophilic aromatic formylation utilizing difluoro(phenylsulfanyl)methane (PhSCF2H) as a formylating agent in hexafluoro-2-propanol (HFIP) as a recyclable ionizing solvent has been developed. The active formylating species was generated via C-F bond cleavage and was characterized to be a bis(phenylsulfanyl)methyl cation by experimental and computational H-1 and C-13 NMR.

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