European Journal of Organic Chemistry

Cover image for Vol. 2012 Issue 34

December 2012

Volume 2012, Issue 34

Pages 6667–6806

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreviews
    6. Short Communications
    7. Full Papers
    8. Correction
    1. You have free access to this content
      Variation of the Viologen Electron Relay in Cyclodextrin-Based Self-Assembled Systems for Photoinduced Hydrogen Evolution from Water (Eur. J. Org. Chem. 34/2012)

      Pablo Contreras Carballada, Nikos Mourtzis, Marco Felici, Sylvestre Bonnet, Roeland J. M. Nolte, René M. Williams, Luisa De Cola and Martin C. Feiters

      Article first published online: 20 NOV 2012 | DOI: 10.1002/ejoc.201290093

      Thumbnail image of graphical abstract

      The cover picture shows how light can be used to generate hydrogen gas from water. The light-harvesting iridium complex, attached to a cyclodextrin, is in the bottom right, and in the top left is the platinum catalyst, with its surface also covered by a cyclodextrin. Responsible for the light-induced electron transfer are the various viologens found in between; one of them, appended with adamantane and bile acid moieties, is shown to be non-covalently bound to cyclodextrins on both the light-harvesting complex and the catalyst. Details of this work are described in the article by M. C. Feiters et al. on p. 6729 ff.

  2. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreviews
    6. Short Communications
    7. Full Papers
    8. Correction
    1. Graphical Abstract: Eur. J. Org. Chem. 34/2012 (pages 6667–6672)

      Article first published online: 20 NOV 2012 | DOI: 10.1002/ejoc.201290095

  3. News

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

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

      Progress in Copper-Mediated Formation of Trifluoromethylated Arenes (pages 6679–6687)

      Tianfei Liu and Qilong Shen

      Article first published online: 27 SEP 2012 | DOI: 10.1002/ejoc.201200648

      Thumbnail image of graphical abstract

      Recent advances in copper-mediated trifluoromethylation of arene substrates are reviewed.

    2. Domino Reactions

      Domino Reactions Initiated by Enantioselective Cu-Catalyzed Conjugate Addition (pages 6688–6695)

      Zuzana Galeštoková and Radovan Šebesta

      Article first published online: 24 SEP 2012 | DOI: 10.1002/ejoc.201200875

      Thumbnail image of graphical abstract

      Copper-catalyzed 1,4-additions of organometallic reagents serve as useful starting points for domino transformations. Initially formed chiral substituted enolates are efficiently trapped with a range of electrophiles. These enolate trapping reactions, preformed either as true domino or as one-pot transformations, significantly broaden the scope of catalytic conjugate additions.

  5. Short Communications

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreviews
    6. Short Communications
    7. Full Papers
    8. Correction
    1. Alkylation of Nitro Derivatives

      Direct and Stereoselective Alkylation of Nitro Derivatives with Activated Alcohols in Trifluoroethanol (pages 6697–6701)

      Diego Petruzziello, Andrea Gualandi, Stefano Grilli and Pier Giorgio Cozzi

      Article first published online: 30 OCT 2012 | DOI: 10.1002/ejoc.201201345

      Thumbnail image of graphical abstract

      We describe the first examples of the reactions of nitro derivatives with benzhydrilic alcohols. The SN1-type reaction is performed in trifluoroethanol as the reaction solvent and is highly compatible with many functional groups. The diastereoselective addition of alcohols to enantioenriched, highly functionalized nitro derivatives also occurs without racemization.

    2. C–H Activation

      Acetamide as Cocatalyst for the Nitrogen-Directed Coupling of Arenes with Aryl Chlorides through Ruthenium-Catalyzed C–H Activation (pages 6702–6706)

      Jie Zhang, Qin Yang, Zhu Zhu, Mao Lin Yuan, Hai Yan Fu, Xue Li Zheng, Hua Chen and Rui Xiang Li

      Article first published online: 30 OCT 2012 | DOI: 10.1002/ejoc.201201127

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      A simple approach for the nitrogen-directed coupling of aromatics with aryl chlorides is described. A series of deactivated aryl chlorides could be coupled smoothly when acetamide was introduced as a cocatalyst.

    3. Supported Palladium Catalysis

      Tsuji–Trost N-Allylation with Allylic Acetates by Using a Cellulose–Palladium Catalyst (pages 6707–6709)

      Buchi Reddy Vaddula, Amit Saha, Rajender S. Varma and John Leazer

      Article first published online: 30 OCT 2012 | DOI: 10.1002/ejoc.201201241

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      Allylic amines were synthesized by N-allylation of primary and secondary amines through a simple and easy procedure involving the use of a heterogeneous cellulose–Pd catalyst; aliphatic and benzylamines underwent facile reaction with substituted and unsubstituted allyl acetates in high yields.

  6. Full Papers

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreviews
    6. Short Communications
    7. Full Papers
    8. Correction
    1. Fine-Tuning of π-Systems

      Bis(azidophenyl)phosphole Building Block for Extended π-Conjugated Systems (pages 6711–6721)

      Wannes Weymiens, František Hartl, Martin Lutz, J. Chris Slootweg, Andreas W. Ehlers, Jos R. Mulder and Koop Lammertsma

      Article first published online: 25 OCT 2012 | DOI: 10.1002/ejoc.201201148

      Thumbnail image of graphical abstract

      We report a novel approach to phosphole-containing π-conjugated materials. From bis(azidophenyl)phosphole 8, a plethora of π-conjugated systems are possible in a single step, incorporating different aromatic capping groups installed using click chemistry. End-group variations introduce photophysical and electronic changes into resulting fluorophores 10, which have been investigated in detail.

    2. Assigning Absolute Stereochemistry

      Absolute Configuration of Highly Flexible Natural Products by the Solid-State ECD/TDDFT Method: Ximaolides and Sinulaparvalides (pages 6722–6728)

      Tibor Kurtán, Rui Jia, Yan Li, Gennaro Pescitelli and Yue-Wei Guo

      Article first published online: 23 OCT 2012 | DOI: 10.1002/ejoc.201200862

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      The absolute configuration of large and flexible macrocyclic natural products is assigned by comparing their solid-state electronic circular dichroism spectra with those calculated using time-dependent density functional theory (TDDFT) methods and X-ray geometry.

    3. Viologen Electron Relay

      Variation of the Viologen Electron Relay in Cyclodextrin-Based Self-Assembled Systems for Photoinduced Hydrogen Evolution from Water (pages 6729–6736)

      Pablo Contreras Carballada, Nikos Mourtzis, Marco Felici, Sylvestre Bonnet, Roeland J. M. Nolte, René M. Williams, Luisa De Cola and Martin C. Feiters

      Article first published online: 4 SEP 2012 | DOI: 10.1002/ejoc.201200886

      Thumbnail image of graphical abstract

      Viologens appended with guest moieties (adamantane or bile acid) for cyclodextrins have been prepared and characterized by (among other techniques) cyclic voltammetry. Their efficiency as electron relays in systems for photocatalytic hydrogen evolution, which are self-assembled from β-cyclodextrin (CD) components, is compared to that of methylviologen.

    4. Dendrimers

      Design and Synthesis of Janus-Type Chiral Dendritic Diphosphanes and Their Applications in Asymmetric Hydrogenation (pages 6737–6744)

      Ji Liu, Yu Feng, Baode Ma, Yan-Mei He and Qing-Hua Fan

      Article first published online: 22 OCT 2012 | DOI: 10.1002/ejoc.201200999

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      A new kind of easily available Janus dendritic diphosphane ligand has been synthesized and their metal complexes were applied to the asymmetric hydrogenation of 2-arylacrylic acids. Interestingly, a clear increase in activity of the dendritic catalysts was observed on going to the higher generations. Furthermore, the third-generation catalyst could be recycled at least five times.

    5. Furo- and Thienoquinolines

      One-Pot Synthesis of Furo- or Thienoquinolines through Sequential Imination and Intramolecular Palladium-Catalyzed Direct Arylation (pages 6745–6751)

      Kassem Beydoun and Henri Doucet

      Article first published online: 25 OCT 2012 | DOI: 10.1002/ejoc.201201142

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      The sequential imination and intramolecular palladium-catalyzed direct arylation of thiophene-3-carbaldehyde or furan-3-carbaldehyde with 2-haloanilines provided a one-pot access to furo- or thienoquinolines in high yields with H2O and HBr as the major waste.

    6. Heterocycle Synthesis

      Iridium-Catalyzed Condensation of Amines and Vicinal Diols to Substituted Piperazines (pages 6752–6759)

      Linda L. R. Lorentz-Petersen, Lars Ulrik Nordstrøm and Robert Madsen

      Article first published online: 23 OCT 2012 | DOI: 10.1002/ejoc.201201099

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      Piperazines are prepared by [Cp*IrCl2]2-catalyzed heterocyclization of 1,2-diols with either 1,2-diamines or primary alkylamines. The reaction is performed in toluene or water and requires no stoichiometric additive. The key step in the mechanism is believed to be the isomerization of an α-hydroxy imine to the corresponding α-amino carbonyl compound.

    7. C–H Bond Activation

      Synthesis of Carbamates by Direct C–H Bond Activation of Formamides (pages 6760–6766)

      Balaji D. Barve, Yang-Chang Wu, Mohamed El-Shazly, Da-Wei Chuang, Yu-Ming Chung, Yi-Hong Tsai, Shou-Fang Wu, Michal Korinek, Ying-Chi Du, Chi-Ting Hsieh, Jeh-Jeng Wang and Fang-Rong Chang

      Article first published online: 22 OCT 2012 | DOI: 10.1002/ejoc.201201160

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      Synthesis of carbamates was accomplished through the reaction of β-keto esters or 2-carbonyl-substituted phenols with formamides using copper chloride and an oxidant. Sixteen aliphatic as well as fourteen aromatic carbamates were prepared in good to excellent yields. The methodology was applied to the synthesis of halogenated carbamates and a carbaryl insecticide derivative.

    8. Three-Component Cycloaddition

      Chemoselective Preparation of Unsymmetrical Bis(1,2,3-triazole) Derivatives and Application in Bis(1,2,3-triazole)-Modified Peptidomimetic Synthesis (pages 6767–6776)

      Teng-fei Niu, Lin Gu, Liang Wang, Wen-bin Yi and Chun Cai

      Article first published online: 22 OCT 2012 | DOI: 10.1002/ejoc.201201096

      Thumbnail image of graphical abstract

      A protocol for the syntheses of unsymmetrical bis(1,2,3-triazole) derivatives has been reported, which utilizes alkynyl-substituted amines as bifunctional linkers to conjoin a copper-free three-component cycloaddition with a copper(I)-catalyzed alkyne–azide cycloaddition in a one-pot procedure. This method was then used to construct unsymmetrical bis(1,2,3-triazole)-modified peptidomimetics.

    9. Olefin Metathesis

      Synthesis of Pyrimidine-Modified NHC Ruthenium-Alkylidene Catalysts and Their Application in RCM, CM, EM and ROMP Reactions (pages 6777–6784)

      Guang-Long Wu, Sheng-Li Cao, Jian Chen and Zili Chen

      Article first published online: 23 OCT 2012 | DOI: 10.1002/ejoc.201200989

      Thumbnail image of graphical abstract

      New N-heterocyclic carbene bearing ruthenium olefin metathesis catalysts were synthesized and applied in various types of olefin metathesis reactions, including ring-closing metathesis, cross-metathesis, enyne metathesis, and ring-opening metathesis polymerization reactions.

    10. Polyguanide Chemistry

      Triguanide Derivatives: Synthesis, Crystal Structure and Evaluation of the Proliferation Effect on Some Tumor Cell Lines (pages 6785–6797)

      Vjekoslav Štrukil, Zoran Glasovac, Ivica Đilović, Dubravka Matković-Čalogović, Lidija Šuman, Marijeta Kralj and Mirjana Eckert-Maksić

      Article first published online: 25 OCT 2012 | DOI: 10.1002/ejoc.201200979

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      The synthesis of new pentasubstituted triguanides 1ae and the spectroscopic characterization of their salts are described. The X-ray structure of the sulfate of compound 1e is also presented. In addition, proliferation assays using five cancer cell lines and acetate salts of 1ae are reported.

    11. Cascade Reactions

      Copper-Catalyzed Cascade Synthesis of 1H-Indolo[1,2-c]quinazoline Derivatives (pages 6798–6803)

      Hao Zhang, Yibao Jin, Hongxia Liu, Yuyang Jiang and Hua Fu

      Article first published online: 23 OCT 2012 | DOI: 10.1002/ejoc.201200953

      Thumbnail image of graphical abstract

      A simple, efficient and practical approach to 1H-indolo[1,2-c]quinazoline derivatives has been developed that uses inexpensive and readily-available catalyst and substrates. The method should provide a new strategy for N-fused heterocycles and will show wide application in organic chemistry and medicinal chemistry.

  7. Correction

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreviews
    6. Short Communications
    7. Full Papers
    8. Correction
    1. You have free access to this content

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