European Journal of Organic Chemistry

Cover image for Vol. 2012 Issue 16

June 2012

Volume 2012, Issue 16

Pages 3031–3179

  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
      Three-Component Coupling of Aldehydes, Amines, and Alkynes Catalyzed by Oxidized Copper Nanoparticles on Titania (Eur. J. Org. Chem. 16/2012)

      María José Albaladejo, Francisco Alonso, Yanina Moglie and Miguel Yus

      Version of Record online: 16 MAY 2012 | DOI: 10.1002/ejoc.201290039

  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. Bioorthogonal Click Protocols

      Nitrile Oxide/Alkyne Cycloadditions – A Credible Platform for Synthesis of Bioinspired Molecules by Metal-Free Molecular Clicking (pages 3043–3058)

      Frances Heaney

      Version of Record online: 13 MAR 2012 | DOI: 10.1002/ejoc.201101823

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      A lofty position will be reserved for nitrile oxide/alkyne cycloadditions amongst the valuable, catalyst-free, bioorthogonal “click” protocols. The future looks bright for the application of NOAC chemistry to contemporary problems in chemical biology and materials science.

    2. Enzymes and Henry Reaction

      Biocatalytic Approaches to the Henry (Nitroaldol) Reaction (pages 3059–3067)

      Sinéad E. Milner, Thomas S. Moody and Anita R. Maguire

      Version of Record online: 12 APR 2012 | DOI: 10.1002/ejoc.201101840

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      Enantiopure β-nitro alcohols are key chiral pool intermediates for the synthesis of a wide array of bioactive molecules. Methods to gain access to these valuable synthons include organo-, transition metal- and bio-catalysis. In recent years biocatalytic methods have gained momentum in this area. This microreview details these advances, which principally include a direct enzyme-catalysed C–C bond formation or enzyme-mediated resolution of the products of the Henry reaction. This approach is reviewed in detail for the first time.

  5. Short Communications

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

      ortho-Olefination of Arylaldehyde O-Methyloximes through Palladium-Catalyzed C–H Activation (pages 3069–3073)

      Zhipeng Xu, Biao Xiang and Peipei Sun

      Version of Record online: 24 APR 2012 | DOI: 10.1002/ejoc.201200393

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      2-Alkenylarylaldehyde O-methyloximes were obtained through palladium(II)-catalyzed ortho-olefination of arylaldehyde O-methyloximes by using O-methyloxime as a directing group in moderate to good yields. Hydrolysis of the coupling products conveniently gave 2-alkenylarylaldehydes.

    2. Binaphthyl-Derived Catalysts

      An Improved and Safer Synthesis of (R)- and (S)-4,4′-Diaminomethyl-BINAP (pages 3074–3078)

      Wissam Dayoub, Alain Favre-Reguillon, Mikael Berthod, Erwann Jeanneau, Gérard Mignani and Marc Lemaire

      Version of Record online: 25 APR 2012 | DOI: 10.1002/ejoc.201200219

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      Previous synthesis of (R)- and (S)-4,4′-diaminomethyl-BINAP was effective, but the method presented several drawbacks including long reaction times and the use of a large excess amount of a harmful reagent. We have developed an improved and safer synthetic route starting from optically active BINAPO.

    3. Heterocyclic Chemistry

      Synthesis of 2,6-Disubstituted Imidazo[2,1-b][1,3,4]thiadiazoles through Cyclization and Suzuki–Miyaura Cross-Coupling Reactions (pages 3079–3083)

      Chloé Copin, Nicolas Henry, Frédéric Buron and Sylvain Routier

      Version of Record online: 23 APR 2012 | DOI: 10.1002/ejoc.201200237

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      The synthesis of 2,6-disubstituted imidazo[2,1-b][1,3,4]thiadiazoles obtained through the cyclization of 2-amino-5-bromo[1,3,4]thiadiazole and several α-halo ketones followed by Suzuki–Miyaura cross-coupling with a variety of boronic acids was developed. The products were obtained in fair to very good yields.

      Corrected by:

      Correction: Synthesis of 2,6-Disubstituted Imidazo[2,1-b][1,3,4]thiadiazoles through Cyclization and Suzuki–Miyaura Cross-Coupling Reactions

      Vol. 2012, Issue 34, 6804–6806, Version of Record online: 25 OCT 2012

    4. Natural Products

      Ruthenium-Catalyzed Cycloisomerization and Its Application to the Synthesis of (±)-Cinchonaminone (pages 3084–3087)

      Takao Ogawa, Tomonori Nakamura, Takuya Araki, Koujirou Yamamoto, Satoshi Shuto and Mitsuhiro Arisawa

      Version of Record online: 26 APR 2012 | DOI: 10.1002/ejoc.201200260

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      Ru-catalyzed cycloisomerization of a 1,3-diene and the alkene of an N-dienyl-2-vinylaniline substrate proceeded smoothly, leading to a 3-exomethylene-2-vinylindole derivative in good yield. This useful synthon was successfully applied to the total synthesis of (±)-cinchonaminone.

    5. Dirhodium(II) Complexes

      Dirhodium(II) Complexes of 2-(Sulfonylimino)pyrrolidine: Synthesis and Application in Catalytic Benzylic Oxidation (pages 3088–3092)

      Abudureheman Wusiman, Xiarepati Tusun and Chong-Dao Lu

      Version of Record online: 23 APR 2012 | DOI: 10.1002/ejoc.201200292

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      The synthesis of dirhodium(II) tetraamidinates derived from 2-(sulfonylimino)pyrrolidines and their use in the catalytic benzylic oxidation are described. A variety of benzylic derivatives, including strongly electron-deficient arylalkanes such as 1-ethyl-4-nitrobenzene, can be readily oxidized by T-HYDRO® in the presence of 1.0 mol-% (3,1)-Rh2(Msip)4 in water under mild reaction conditions.

  6. Full Papers

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

      Three-Component Coupling of Aldehydes, Amines, and Alkynes Catalyzed by Oxidized Copper Nanoparticles on Titania (pages 3093–3104)

      María José Albaladejo, Francisco Alonso, Yanina Moglie and Miguel Yus

      Version of Record online: 15 MAR 2012 | DOI: 10.1002/ejoc.201200090

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      A3 coupling catalyzed by ultrafine copper nanoparticles on titania under solvent-free conditions is described. Some examples of KA2 coupling are also reported. The catalyst is reusable and exhibited better performance than commercially available copper catalysts. The participation of copper(I) acetylides in a heterogeneous process has been demonstrated.

    2. Selective N-Alkylation of Arylamines with Alkyl Chloride in Ionic Liquids: Scope and Applications (pages 3105–3111)

      Antonio Monopoli, Pietro Cotugno, Marina Cortese, Cosima Damiana Calvano, Francesco Ciminale and Angelo Nacci

      Version of Record online: 16 APR 2012 | DOI: 10.1002/ejoc.201200202

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      A protocol for the selective N-alkylation of primary aromatic amines in tetraalkylammonium ionic liquids was developed. This approach complements existing strategies by broadening the scope with more challenging substrates (e.g., p-nitroaniline) and alkylating agents (chloroalkane).

    3. Homogeneous Catalysis

      Diels–Alder Reactions for the Construction of Cyclopropylarenes (pages 3112–3121)

      Marion Arndt, Gerhard Hilt, Alexander F. Khlebnikov, Sergei I. Kozhushkov and Armin de Meijere

      Version of Record online: 17 APR 2012 | DOI: 10.1002/ejoc.201200105

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      The application of cyclopropyl-substituted alkynes and 1,3-dienes in cobalt-catalyzed Diels–Alder reactions led to various cyclopropyl-substituted arenes. In only one case, the ring-opened product was isolated. This shows that the cyclopropyl subunits were generally compatible with the conditions of the cobalt catalysis and of the subsequent DDQ oxidation of the dihydroaromatic intermediates.

      Corrected by:

      Addendum/Correction: Diels–Alder Reactions for the Construction of Cyclopropylarenes

      Vol. 2013, Issue 6, 1171–1172, Version of Record online: 21 JAN 2013

    4. Glycosyl Donors

      Methyl 1,2-Orthoesters as Useful Glycosyl Donors in Glycosylation Reactions: A Comparison with n-Pent-4-enyl 1,2-Orthoesters (pages 3122–3131)

      Clara Uriel, Juan Ventura, Ana M. Gómez, J. Cristóbal López and Bert Fraser-Reid

      Version of Record online: 12 APR 2012 | DOI: 10.1002/ejoc.201200089

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      Methyl 1,2-orthoesters are useful glycosyl donors upon acid activation with boron trifluoride etherate. They react smoothly with monosaccharide alcohols or diols, leading to disaccharides in good to excellent yields. When monosaccharide diols are used as glycosyl acceptors, good regioselectivity in the glycosyl coupling is observed.

    5. Rearrangement vs. Aryne Formation

      Attempts Directed towards the Synthesis of Intermediate (Aryne)chromium Complexes from Aryl Triflates and from (Haloarene)chromium Complexes (pages 3132–3141)

      Georg Werner and Holger Butenschön

      Version of Record online: 20 APR 2012 | DOI: 10.1002/ejoc.201200176

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      Electron-rich (phenyl triflate)chromium complexes show an unexpectedly high propensity for anionic thia-Fries rearrangements, which take place at –78 °C with very high yields. Unlike in the case of the uncomplexed ligands, no aryne formation was observed.

    6. Substituted 2,3-Dihydrofurans

      Preparation of (E)-4-Aryl-1,1,1-trifluoro-3-tosylbut-3-en-2-ones as Fluorinated Building Blocks and Their Application in Ready and Highly Stereoselective Routes to trans-2,3-Dihydrofurans Substituted with Trifluoromethyl and Sulfonyl Groups (pages 3142–3150)

      Haigang Yu, Jing Han, Jie Chen, Hongmei Deng, Min Shao, Hui Zhang and Weiguo Cao

      Version of Record online: 12 APR 2012 | DOI: 10.1002/ejoc.201200180

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      (E)-4-Aryl-1,1,1-trifluoro-3-tosylbut-3-en-2-ones were prepared through a two-step process and used as fluorinated building blocks in the stereoselective preparation of a series of 4-tosyl-5-trifluoromethyl-trans-2,3-dihydrofuran derivatives with the assistance of arsonium ylides.

    7. Functionalized NHC Ligands

      Heck–Matsuda Reactions Catalyzed by a Hydroxyalkyl-Functionalized NHC and Palladium Acetate (pages 3151–3156)

      Itziar Peñafiel, Isidro M. Pastor and Miguel Yus

      Version of Record online: 23 APR 2012 | DOI: 10.1002/ejoc.201200181

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      A hydroxy-functionalized NHC in combination with a palladium source allows the Heck–Matsuda reaction to be carried out between different arenediazonium salts and various alkenes (i.e., acrylates, acrylamide, styrene, and cyclohexene) The optimal conditions to perform the reaction were determined by a design of experiments study.

    8. Molecular Diversity

      Molecular Diversity of Three-Component Reactions of N-Benzylbenzimidazolium Salts, Isatin, and Malononitrile or Ethyl Cyanoacetate (pages 3157–3164)

      Li Hui, Hong-Yan Li and Chao-Guo Yan

      Version of Record online: 23 APR 2012 | DOI: 10.1002/ejoc.201200269

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      The three-component reactions of N-benzylbenzimidazolium salts, isatins, and malononitrile or ethyl cyanoacetate showed very interesting molecular diversity depending on the structures of the benzimidazolium salts: zwitterionic or ring-opened products were obtained.

    9. Oxidative Dimerization

      6,12-Diphenyldibenzo[b,f][1,5]diazocine as an Electron-Capture Agent: Efficient Mechanistic Probe for SET Processes and Reagent for the Oxidative Dimerization of Benzylic Organometallics (pages 3165–3171)

      John J. Eisch, Kun Yu and Arnold L. Rheingold

      Version of Record online: 20 APR 2012 | DOI: 10.1002/ejoc.201200278

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      6,12-Diphenyldibenzo[b,f][1,5]diazocine readily undergoes transannular SET reductions with sodium, lithium, or even benzylic lithium or magnesium reagents to yield, upon hydrolysis, 4b,9b-diphenyl-4b,5,9b,10-tetrahydroindolo[3,2-b]indole. This diazocine can thereby serve as a mechanistic probe for SET processes and as a reagent for the oxidative dimerization of benzylic organometallics.

    10. Nucleoside Derivatives

      Synthesis of 2′,3′-Dideoxy-2′-fluoro-3′-(hydroxyimino)-, -3′-(methoxyimino)- and -3′-(hydroxyamino)pyrimidine Nucleosides (pages 3172–3179)

      Ahmed Khalil, Christophe Mathé and Christian Périgaud

      Version of Record online: 18 APR 2012 | DOI: 10.1002/ejoc.201200119

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      The title pyrimidine nucleosides were prepared from their respective 2′,3′-dideoxy-2′-fluoro parent nucleosides, and structural assignments were made based upon their 1H and 19F NMR spectra. Antiviral and antitumor activities were evaluated, but none of the target nucleosides showed antiviral properties, except for compound 19, which showed moderate cytotoxic activity.

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