European Journal of Organic Chemistry

Cover image for Vol. 2012 Issue 19

July 2012

Volume 2012, Issue 19

Pages 3531–3696

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
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      Highly Selective Primary Alkoxycarboxylation and Esterification of Unprotected Pyranose Derivatives Mediated by Scandium(III) Triflate Catalysis (Eur. J. Org. Chem. 19/2012)

      Michael S. McClure, Malcolm B. Berry, Darren Caine, Claire Crawford, Brian C. Crump, Bobby N. Glover, Sandeep B. Kedia, Alan Millar, Mark B. Mitchell, Christopher J. Nichols, Daniel E. Patterson and Jeremiah Powers

      Version of Record online: 20 JUN 2012 | DOI: 10.1002/ejoc.201290048

  2. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
  3. News

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
  4. Microreview

    1. Top of page
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    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
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    1. Multicomponent Reactions

      Recent Advances in Asymmetric Isocyanide-Based Multicomponent Reactions (pages 3543–3559)

      Sander S. van Berkel, Berry G. M. Bögels, Marloes A. Wijdeven, Bernhard Westermann and Floris P. J. T. Rutjes

      Version of Record online: 27 MAR 2012 | DOI: 10.1002/ejoc.201200030

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      This review discusses the use of various isocyanides (regular, chiral, and convertible) in asymmetric multicomponent reactions. In particular, stereoselective Ugi and Passerini reactions are highlighted, as well as their applications in modular sequential reactions and natural product synthesis.

  5. Short Communications

    1. Top of page
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    3. Graphical Abstract
    4. News
    5. Microreview
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    1. Sc-Catalyzed Alkoxycarboxylations

      Highly Selective Primary Alkoxycarboxylation and Esterification of Unprotected Pyranose Derivatives Mediated by Scandium(III) Triflate Catalysis (pages 3561–3565)

      Michael S. McClure, Malcolm B. Berry, Darren Caine, Claire Crawford, Brian C. Crump, Bobby N. Glover, Sandeep B. Kedia, Alan Millar, Mark B. Mitchell, Christopher J. Nichols, Daniel E. Patterson and Jeremiah Powers

      Version of Record online: 8 MAY 2012 | DOI: 10.1002/ejoc.201200261

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      A novel Sc-catalyzed alkoxycarboxylation and esterification reaction of unprotectedpyranose substrates is described. This method gives nearly complete selectivity compared with existing methods and avoids known problems with polycarboxylation/acylation. A preliminary mechanistic model is proposed.

    2. Ion Exchange

      Efficient Method for Varying the Anions in Quaternary Onium Halides (pages 3566–3569)

      Jong Yeob Jeon, Jobi Kodiyan Varghese, Ji Hae Park, Suck-Hyun Lee and Bun Yeoul Lee

      Version of Record online: 18 MAY 2012 | DOI: 10.1002/ejoc.201200370

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      An efficient and scalable method for the conversion of quaternary onium halides into the corresponding salts of various anions [NO3, BF4, PF6, CF3SO3, CH3SO3, ClO4, pTsO, CF3CO2, 2,4-(NO2)2C6H3O] is disclosed.

    3. Molecular Recognition

      Monitoring Fluoride Binding in DMSO: Why is a Singular Binding Behavior Observed? (pages 3570–3574)

      Matthieu Goursaud, Paolo De Bernardin, Antonella Dalla Cort, Kristin Bartik and Gilles Bruylants

      Version of Record online: 18 MAY 2012 | DOI: 10.1002/ejoc.201200165

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      The titration behavior for fluoride binding in DMSO can often not be ascribed to a classical 1:1 binding isotherm. The culprit can be water, which leads to the generation of other species that can interact with the molecular receptor. The plethora of equilibria to be considered makes the quantitative evaluation of fluoride binding extremely perilous.

    4. Cross-Coupling

      An Efficient Suzuki–Miyaura Coupling of Aryl Sulfamates and Boronic Acids Catalyzed by NiCl2(dppp) (pages 3575–3579)

      Guo-Jun Chen and Fu-She Han

      Version of Record online: 29 MAY 2012 | DOI: 10.1002/ejoc.201200444

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      The NiCl2(dppp)-catalyzed Suzuki–Miyaura cross-coupling of aryl sulfamates and boronic acids was investigated. NiCl2(dppp) was found to be a highly active and general catalyst that can be used in small quantities (1.0–1.5 mol-%). The method displays broad generality not only to various aryl sulfamates, but also to an array of boronic acids. Furthermore, various functional groups are tolerated.

  6. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    1. Donor–Acceptor Systems

      A Straightforward Electroactive π-Extended Tetrathiafulvalene (exTTF) Building Block (pages 3581–3586)

      Agustín Molina-Ontoria, Raúl García, Andreas Gouloumis, Francesco Giacalone, M. Rosario Torres and Nazario Martín

      Version of Record online: 22 MAY 2012 | DOI: 10.1002/ejoc.201200115

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      The synthesis and X-ray structure of a new and readily available exTTF derivative bearing a methyltriphenylphosphonium bromide moiety as a new building block for the construction of electroactive molecules is described.

    2. Annulation Reaction Mechanism

      Reaction Mechanism of Phosphane-Catalyzed [4+2] Annulations between α-Alkylallenoates and Activated Alkenes: A Computational Study (pages 3587–3597)

      Lili Zhao, Mingwei Wen and Zhi-Xiang Wang

      Version of Record online: 18 MAY 2012 | DOI: 10.1002/ejoc.201200121

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      This DFT study reveals that the water-aided [3+2] addition and direct [4+2] addition mechanisms are both feasible for the titled [4+2] annulations. Unlike typical [3+2] annulations, which require water as hydrogen transfer mediator, [4+2] annulation can occur without additional mediator because the carbon bearing nitrile groups can act as the hydrogen transfer mediator.

    3. Asymmetric Organocatalysis

      Cinchona Alkaloid Catalyzed Regio- and Enantioselective Allylic Amination of Morita–Baylis–Hillman Carbonates with Isatins (pages 3598–3606)

      Mei-Xin Zhao, Ming-Xiao Chen, Wen-Hao Tang, Deng-Ke Wei, Tong-Lei Dai and Min Shi

      Version of Record online: 31 MAY 2012 | DOI: 10.1002/ejoc.201200376

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      We have developed an efficient regio- and enantioselective allylic amination of MBH carbonates with isatins by using commercially available, modified cinchona alkaloids as organocatalysts under mild conditions. The allylic amination products were obtained by a tandem SN2′/SN2′ reaction in good yields (46–74 %), high regioselectivities, and good enantioselectivities (up to 89 % ee).

    4. Natural Products

      Heck–Matsuda Arylation as a Strategy to Access Kavalactones Isolated from Polygala sabulosa, Piper methysticum, and Analogues (pages 3607–3616)

      Cristian Soldi, Angélica V. Moro, Moacir G. Pizzolatti and Carlos R. D. Correia

      Version of Record online: 22 MAY 2012 | DOI: 10.1002/ejoc.201200308

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      The Heck–Matsuda reaction was applied to the syntheses of three bioactive pyrones isolated from Polygala sabulosa, eight kavalactones isolated from Piper methysticum, and several kavalactone analogues.

    5. Heterocyclic Synthesis

      Transition-Metal-Catalyzed Hydroamination and Carboamination Reactions of Anthranilic Allenamides as a Route to 2-Vinyl- and 2-(α-Styryl)quinazolin-4-one Derivatives (pages 3617–3624)

      Gianluigi Broggini, Elena Borsini, Andrea Fasana, Giovanni Poli and Frédéric Liron

      Version of Record online: 22 MAY 2012 | DOI: 10.1002/ejoc.201200353

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      Intramolecular transition-metal-catalyzed reactions of allenamides have been proven to be useful tools for accessing 2-vinyl- and 2-(α-styryl)quinazolin-4-ones. The two types of products were obtained by simple switching of the catalytic system, namely, gold-catalyzed hydroamination and palladium-catalyzed carboamination furnished 2-vinyl- and 2-(α-styryl)-substituted quinazolinones, respectively.

    6. Recyclable NHC Catalysts

      Recyclable Hybrid Silica-Based Catalysts Derived from Pd–NHC Complexes for Suzuki, Heck and Sonogashira Reactions (pages 3625–3635)

      Guadalupe Borja, Amàlia Monge-Marcet, Roser Pleixats, Teodor Parella, Xavier Cattoën and Michel Wong Chi Man

      Version of Record online: 23 MAY 2012 | DOI: 10.1002/ejoc.201200205

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      New hybrid silica materials derived from NHC-palladium complexes have been prepared by a sol-gel process and efficiently applied as recyclable catalysts in C–C coupling reactions.

    7. Enamination Reactions

      Efficient N-Alkyl Enamination of 3-(Thiobenzoyl)pyrrolo[2,3-b]quinoxalin-2-one, E/Z Isomerisation of the Reaction Products and Potential Fluorescent Sensors for ­Zinc(II) Ion (pages 3636–3646)

      Katarzyna Ostrowska, Edyta Piegza, Maria Rąpała-Kozik and Katarzyna Stadnicka

      Version of Record online: 22 MAY 2012 | DOI: 10.1002/ejoc.201200211

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      An efficient N-alkyl enamination is reported as a convenient method for the insertion of metal-ion receptor units into a fluorescent indicator. New E/Z push–pull olefins have been characterised. The interconversion of the E into the Z forms and their equilibrium in [D6]DMSO were studied. Addition of zinc ions to the non-fluorescent free bases leads to fluorescent emission of the probes.

    8. 1,2-Diaroylbenzenes

      Oxidative Ring Opening of 1,3-Diarylbenzo[c]heterocycles Using m-CPBA: Preparation of 1,2-Diaroylbenzenes (pages 3647–3657)

      Meganathan Nandakumar, Ramakrishnan Sivasakthikumaran and Arasambattu K. Mohanakrishnan

      Version of Record online: 23 MAY 2012 | DOI: 10.1002/ejoc.201200311

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      An efficient procedure for the preparation of a variety of unsymmetrical 1,2-diaroylbenzenes was achieved at room temperature through a m-CPBA-mediated oxidative cleavage of benzo[c]furan analogs. The oxidative ring-opening reaction with benzo[c]thiophene and benzo[c]selenophene analogs was also successful.

    9. Cholesterol Solubilization

      Synthesis of Cholic Acid Oligomer–Taurine Conjugates: A Study of Their Aggregation and Cholesterol Solubilization (pages 3658–3664)

      T. B. N. Satyanarayana, Uday Maitra and A. J. Savyasachi

      Version of Record online: 31 MAY 2012 | DOI: 10.1002/ejoc.201200312

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      Two cholic acid tetramer–taurine conjugates, in which the bile acid units were connected through their side chains, were synthesized. Their aggregation in water/alcohol mixtures were characterized by light scattering and electron microscopy studies. Cooperative effects in the dissolution of cholesterol were evaluated and showed enhanced efficiency of the tetramer over the monomer.

    10. Nucleoside Synthesis

      Solid-Phase Synthesis of 5′-O-[N-(Acyl)sulfamoyl]adenosine Derivatives (pages 3665–3669)

      Itedale Namro Redwan, Hanna Jacobson Ingemyr, Thomas Ljungdahl, Christopher P. Lawson and Morten Grøtli

      Version of Record online: 16 MAY 2012 | DOI: 10.1002/ejoc.201200329

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      A novel and straightforward solid-phase protocol for the parallel synthesis of 5′-O-[N-(acyl)sulfamoyl]adenosines has been developed. The synthetic protocol enables the possibility of variation of the acyl group attached to the sulfamoyl moiety. Variation of the acyl group provides compounds useful for studies of various biological activities.

    11. Aqueous Suzuki–Miyaura Coupling

      Oxime–Palladacycle-Catalyzed Suzuki–Miyaura Arylation and Alkenylation of Aryl Imidazolesulfonates under Aqueous and Phosphane-Free Conditions (pages 3670–3676)

      José Francisco Cívicos, Diego A. Alonso and Carmen Nájera

      Version of Record online: 22 MAY 2012 | DOI: 10.1002/ejoc.201200368

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      The title sulfonates are cross-coupled in high yields with aryl- and alkenylboronic acids and potassium trifluoroborates byusing oxime–palladacycles in water under microwave irradiation. One-pot phenol sulfonylation and Suzuki coupling as well as allows orthogonal functionalization of bifunctionalized aryl derivatives are allowed.

    12. Fused Pyrazoles

      Synthesis of Diverse Fused Pyrazoles through Palladium-Mediated Heteroarylation of Heteroarene C–H Bonds (pages 3677–3683)

      Maloy Nayak and Sanjay Batra

      Version of Record online: 22 MAY 2012 | DOI: 10.1002/ejoc.201200401

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      The facile and efficient synthesis of annulated pyrazoles through the Pd(OAc)2-mediated heteroarylation of heteroarene C–H bonds in substrates derived from the Morita–Baylis–Hillman reaction adducts of 4-iodopyrazolecarbaldehydes is described.

    13. Heterocycles

      Base-Promoted Heterocyclization of Fluorinated Alkynylphosphonates with Select ortho-Aminobenzonitriles (pages 3684–3690)

      Blazej Duda, Sergey N. Tverdomed, Boris I. Ionin and Gerd-Volker Röschenthaler

      Version of Record online: 23 MAY 2012 | DOI: 10.1002/ejoc.201200379

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      The syntheses of various CF2-containing (4-aminoquinolin-3-yl)phosphonates have been reported. The reaction proceeded well by using K2CO3 as the basic mediator in refluxing toluene as the solvent.

    14. Organocatalysis

      Enantioselective Asymmetric Michael Addition of Cyclic Diketones to β,γ-Unsaturated α-Keto Esters (pages 3691–3696)

      Yi-Feng Wang, Ke Wang, Wei Zhang, Bin-Bin Zhang, Chi-Xiao Zhang and Dan-Qian Xu

      Version of Record online: 23 MAY 2012 | DOI: 10.1002/ejoc.201200179

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      The Michael addition of cyclic diketones to β,γ-unsaturated α-keto esters catalyzed by bifunctional squaramide-derived chiral catalysts to afford adducts in high yields (up to 95 %) and excellent enantioselectivities (up to 99 % ee) under mild conditions is reported. The reaction affords chiral Michael adducts, which are important moieties in the skeletons of biological and pharmaceutical molecules.

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