European Journal of Organic Chemistry

Cover image for Vol. 2013 Issue 2

January 2013

Volume 2013, Issue 2

Pages 203–406

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreviews
    6. Short Communications
    7. Full Papers
    1. You have free access to this content
      Synthesis of Functionalized, Sterically Congested Calix[4]phyrin Macrocycles Using Donor–Acceptor-Substituted Cyclopropanes – First Example of a Mono-meso-spirolactone Incorporated into a Calix[4]phyrin (Eur. J. Org. Chem. 2/2013)

      M. Hassan Beyzavi, Dieter Lentz, Hans-Ulrich Reissig and Arno Wiehe

      Version of Record online: 2 JAN 2013 | DOI: 10.1002/ejoc.201390000

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      The cover picture shows a new, stepwise synthesis of oxidation-resistant meso-hydrogenated calix[4]phyrins using a donor–acceptor-substituted cyclopropane precursor. This approach allows a variable substitution in the residues of their sp2-meso centers without the need for a porphyrin intermediate. Among the three different stereoisomers (syn-equatorial, syn-axial and anti) of these “roof-like” macrocycles in the solid state, the yn-axial is generally the most stable one. Details are discussed in the article by H.-U. Reissig, A. Wiehe et al. on p. 269 ff. We thank M. Sc. Eng. Ehsan Fereidoonnezhad for his contribution to the cover picture design.

  2. Graphical Abstract

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

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

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

      Thienannulation: Efficient Synthesis of π-Extended Thienoacenes Applicable to Organic Semiconductors (pages 217–227)

      Kazuo Takimiya, Masahiro Nakano, Myeong Jin Kang, Eigo Miyazaki and Itaru Osaka

      Version of Record online: 6 NOV 2012 | DOI: 10.1002/ejoc.201201139

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      Versatile and efficient thiophene-annulation reactions on aromatic cores, termed “thienannulation reactions”, are described. Those thienannulation reactions have been the driving force behind the recent development of new thienoacene-based organic semiconductors applicable to high-performance organic field-effect transistors.

    2. 2,1,3-Benzothiadiazole Fluorophores

      2,1,3-Benzothiadiazole and Derivatives: Synthesis, Properties, Reactions, and Applications in Light Technology of Small Molecules (pages 228–255)

      Brenno A. D. Neto, Alexandre A. M. Lapis, Eufrânio N. da Silva Júnior and Jairton Dupont

      Version of Record online: 7 DEC 2012 | DOI: 10.1002/ejoc.201201161

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      Molecular 2,1,3-benzothiadiazole (BTD) is an important nucleus used in the chemistry of photoluminescent compounds and applicable for light technology. Its properties and chemical reactivity are fundamental for the design of organic electronic devices. BTD derivatives can be used as constituents of organic light-emitting diodes, solar cells, liquid crystals, dyes, photovoltaic cells and many others, and these compounds represent an exciting area of study.

  5. Short Communications

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreviews
    6. Short Communications
    7. Full Papers
    1. Copper-Catalyzed Coupling

      One-Pot Synthesis of Symmetrical Diaryl Trithiocarbonates through Copper-Catalyzed Coupling of Aryl Compounds, Sodium Sulfide, and Carbon Disulfide (pages 257–259)

      Mohammad Gholinejad

      Version of Record online: 26 NOV 2012 | DOI: 10.1002/ejoc.201201126

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      A protocol for the synthesis of symmetrical diaryl trithiocarbonates through the one-pot copper-catalyzed coupling reaction of sodium sulfide, carbon disulfide, and aryl compounds is presented.

    2. Domino Reactions

      Intramolecular Cascade Hydroarylation/Cycloisomerization Strategy for the Synthesis of Polycyclic Aromatic and Heteroaromatic Systems (pages 260–263)

      Jan Storch, Martin Bernard, Jan Sýkora, Jindřich Karban and Jan Čermák

      Version of Record online: 19 NOV 2012 | DOI: 10.1002/ejoc.201201329

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      A model study towards the synthesis of helical compounds through a platinum-catalyzed cascade cycloisomerization reaction is described. The reaction is successfully applied to the preparation of tetracyclic helical systems. Attempts for higher analogues are also included.

    3. Heteroannulation

      Thermal Rearrangement of Azido Ketones into Oxazoles via Azirines: One-Pot, Metal-Free Heteroannulation to Functionalized 1,3-Oxazoles (pages 264–267)

      Shailesh R. Shah, Sudhanva S. Navathe, Amol G. Dikundwar, Tayur N. Guru Row and Andrea T. Vasella

      Version of Record online: 26 NOV 2012 | DOI: 10.1002/ejoc.201201269

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      In a one-pot synthesis, α-bromoacetophenones were converted into 2-aryl-1,3-oxazole-4-carbaldehydes. An unprecedented rearrangement of the carbon framework was observed. The transformation was studied in detail and a viable mechanism was proposed on the basis of the observations and the intermediates isolated.

  6. Full Papers

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

      Synthesis of Functionalized, Sterically Congested Calix[4]phyrin Macrocycles Using Donor–Acceptor-Substituted Cyclopropanes – First Example of a Mono-meso-spirolactone Incorporated into a Calix[4]phyrin (pages 269–282)

      M. Hassan Beyzavi, Dieter Lentz, Hans-Ulrich Reissig and Arno Wiehe

      Version of Record online: 6 DEC 2012 | DOI: 10.1002/ejoc.201201295

      Thumbnail image of graphical abstract

      A new stepwise synthesis of oxidation-resistant meso-hydrogenated calix[4]phyrins is reported, which allows variable substitution in the residues of their sp2-meso-centers without the need for a porphyrin intermediate. Of special interest is an unprecedented example of an acid-driven lactonization that results in a mono-meso-spirolactone incorporated into a calix[4]phyrin(1.1.1.1).

    2. Microporous Materials

      Synthesis and Topological Determination of Hexakis-Substituted 1,4-Ditritylbenzene and Nonakis-Substituted 1,3,5-Tritritylbenzene Derivatives: Building Blocks for Higher Supramolecular Assemblies (pages 283–299)

      Oliver Plietzsch, Alexandra Schade, Andreas Hafner, Juhani Huuskonen, Kari Rissanen, Martin Nieger, Thierry Muller and Stefan Bräse

      Version of Record online: 27 NOV 2012 | DOI: 10.1002/ejoc.201201162

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      Short, high-yielding syntheses of 1,4-ditrityl- and 1,3,5-tritritylbenzene on gram scales are described. Both can be functionalized in six- and nine-fold reactions, respectively, to obtain building blocks for supramolecular architectures. The 1,4-ditritylbenzene skeleton has been expanded by formal intercalation of acetylene units leading to a larger molecular tecton.

    3. Perylenetetracarboxdiimide Dyes

      Core Expansion of Perylenetetracarboxdiimide Dyes with Anthraquinone Units for Electron-Accepting Materials (pages 300–306)

      Liang Xu, Chao Liu, Zhihong Qin, Runsheng Jiang and Yongjun Li

      Version of Record online: 26 NOV 2012 | DOI: 10.1002/ejoc.201200980

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      Phototriggered intramolecular cyclization of 2-anthraquinone-substituted perylenetetracarboxdiimide produced a novel core-expanded perylenetetracarboxdiimide chromophore. Their properties were investigated by optical absorption spectroscopy, electrochemistry, and theoretical calculations, and excellent electron-accepting abilities were observed.

    4. Asymmetric Hydrosilylation

      Mechanism and Enantioselectivity of [Zinc(diamine)(diol)]-Catalyzed Asymmetric Hydrosilylation of Ketones: DFT, NMR and ECD Studies (pages 307–318)

      Jadwiga Gajewy, Jacek Gawronski and Marcin Kwit

      Version of Record online: 22 NOV 2012 | DOI: 10.1002/ejoc.201200992

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      Asymmetric induction in hydrosilylation of acetophenone catalyzed by [Zn(chiral diamine)(diol)] complexes is rationalized with the aid of DFT calculations combined with 1H NMR and ECD measurements. The favored S-configuration of the product with (R,R)-configured ligand is the result of hydride transfer from activated Zn complex to the re face of the N–H···O=C hydrogen bonded carbonyl substrate.

    5. Phosphonation of Aryl Halides

      Synthesis of Aryl and Arylmethyl Phosphonates by Cross-Coupling of Aryl or Arylmethyl Halides (X = I, Br and Cl) with Diisopropyl H-Phosphonate (pages 319–325)

      Kai Xu, Hao Hu, Fan Yang and Yangjie Wu

      Version of Record online: 20 NOV 2012 | DOI: 10.1002/ejoc.201201230

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      A new method is presented for the synthesis of aryl and arylmethyl phosphonates by palladacycle-catalysed phosphonation of aryl halides or by the K2CO3-promoted cross-coupling of arylmethyl halides with H-phosphonate. The substrate scope could be extended to inactive electron-rich aryl chlorides.

    6. Electrochemical Transesterification

      Electrogenerated N-Heterocyclic Carbenes in the Room Temperature Parent Ionic Liquid as an Efficient Medium for Transesterification/Acylation Reactions (pages 326–331)

      Isabella Chiarotto, Marta Feroci, Giovanni Sotgiu and Achille Inesi

      Version of Record online: 12 NOV 2012 | DOI: 10.1002/ejoc.201201023

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      An efficient transesterification reaction has been carried out in Bmim-BF4 ionic liquid, using an electrogenerated NHC as catalyst. The catalyst was obtained by cathodic reduction of the ionic liquid under galvanostatic conditions. The product yields are high and valuable nicotinate esters are obtained.

    7. Natural Product Synthesis

      Synthesis of Isobavachalcone and Some Organometallic Derivatives (pages 332–347)

      John P. Grealis, Helge Müller-Bunz, Yannick Ortin, Michael Casey and Michael J. McGlinchey

      Version of Record online: 9 NOV 2012 | DOI: 10.1002/ejoc.201201063

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      Isobavachalcone, a prenylated chalcone that has broad biological activity, in particular against neuroblastomas, is normally isolated in very low yields from Psoralea corylifolia (shown in the picture). It has now been synthesised in five steps in an overall yield of 15 %. Moreover, several organometallic sandwich derivatives containing iron, ruthenium or cobalt have also been prepared.

    8. Synthesis and Configuration of the Phenolic Nonadecanediol Isolated from the Resinous Exudates of Heliotropium sinuatum (pages 348–355)

      Chao-Yuan Chen, Shao-Min Zhang, Yikang Wu and Po Gao

      Version of Record online: 20 NOV 2012 | DOI: 10.1002/ejoc.201201184

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      The (3S,5R) and (3R,5R) isomers of the title phenol-diol, a natural antioxidant, were synthesized following chiral-pool-based routes. Comparison of the 1H and 13C NMR spectra, rotations, and melting points for the natural and the synthetic samples showed that the natural product has a (3S,5R) configuration. Some changes in 13C NMR data and optical rotation caused by CD3OD were observed.

    9. Total Synthesis

      Chemoenzymatic Asymmetric Total Synthesis of (R)-Lasiodiplodin Methyl Ether through a Sulfatase-Based Deracemization Process (pages 356–361)

      Michael Fuchs, Michael Toesch, Markus Schober, Christiane Wuensch and Kurt Faber

      Version of Record online: 27 NOV 2012 | DOI: 10.1002/ejoc.201201296

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      Lasiodiplodin methyl ether, a precursor of the antileukemic agent lasiodiplodin, was synthesized through a seven-step chemoenzymatic route. The central chiral building block was obtained through a sulfatase-based deracemization protocol, which furnished a single stereoisomer in 93 % ee from the racemate.

    10. Host-Guest Systems

      Polyglycerol-Tagged Molecular Clips as Receptors in Protic Solvents (pages 362–367)

      Maximilian Zieringer, Marçal Casas Cartagena, Ewelina Burakowska, Johannes Taktikos, Katja Neuthe, Heinz Bandmann, Frank-Gerrit Klärner and Rainer Haag

      Version of Record online: 13 NOV 2012 | DOI: 10.1002/ejoc.201200345

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      Dendronized molecular clips with polyglycerol substituents increase their solubility in protic solvents. Such clips can mimic natural receptors in binding and carrying of biologically relevant substrates. The nature of the substituents dramatically affects the association behavior of molecular clips and several substrates in protic solvents. These effects are quantified by 1H NMR titration.

    11. Heterocyclic Chemistry

      One-Pot Synthesis of N-(Imidazo[1,2-a]pyridin-3-yl)- and N-(Imidazo[2,1-b][1,3]thiazol-5-yl)sulfonamides (pages 368–375)

      Igor B. Rozentsveig, Valery Y. Serykh, Gulnur N. Chernysheva, Kirill A. Chernyshev, Evgeniy V. Kondrashov, Evgeny V. Tretyakov and Galina V. Romanenko

      Version of Record online: 12 NOV 2012 | DOI: 10.1002/ejoc.201201006

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      2-Aminopyridines or 2-aminothiazole easily react with electrophilic arenesulfonyl imines to give the corresponding addition products of the amine moiety to the azomethine group. The obtained compounds were successfully used to synthesize (imidazo[1,2-a]pyridin-3-yl)sulfonamides and (imidazo[2,1-b][1,3]thiazol-5-yl)sulfonamides in a domino manner.

    12. Natural Product Synthesis

      The Formal Total Synthesis of FR252921 – An Immunosuppressant (pages 376–388)

      J. S. Yadav and Sandip Sengupta

      Version of Record online: 15 NOV 2012 | DOI: 10.1002/ejoc.201201097

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      The formal total synthesis of FR252921 is described. The key steps include the preparation of three fragments starting from 1,4-butanediol, (R)-malic acid, and prenol, respectively, followed by two consecutive peptide couplings of the three fragments.

    13. Annulation Reactions

      Dihydropyridazine Derivatives with Cyclopenta-, Benzo-, Furo-, Thiopyrano- and Pyrido-Annulation (pages 389–400)

      Miriam Penning and Jens Christoffers

      Version of Record online: 26 NOV 2012 | DOI: 10.1002/ejoc.201201158

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      Depending on the reaction conditions, regioisomeric, annulated dihydropyridazines are formed from 1,4-diketones and arylhydrazines.

    14. Trifluoromethylated Heterocycles

      Highly Efficient Construction of Trifluoromethylated Heterocycles; [3+2] Annulation of N,N′-Cyclic or C,N-Cyclic Azomethine Imines with Trifluoromethyl-Containing Electron-Deficient Olefins (pages 401–406)

      De Wang, Hong-Ping Deng, Yin Wei, Qin Xu and Min Shi

      Version of Record online: 9 NOV 2012 | DOI: 10.1002/ejoc.201201244

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      A highly regio- and stereoselective synthesis of pyrazolidine analogues has been developed, affording highly functionalized trifluoromethyl-containing pyrazolidine analogues in excellent yields, with high diastereoselectivities, under mild conditions.

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