European Journal of Organic Chemistry

Cover image for Vol. 2015 Issue 19

July 2015

Volume 2015, Issue 19

Pages 4039–4268

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    1. You have free access to this content
      Dihydroazulene/Vinylheptafulvene Photoswitch: Ultrafast Back Reaction Induced by Dihydronaphthalene Annulation (Eur. J. Org. Chem. 19/2015)

      Søren Lindbæk Broman, Oleg Kushnir, Martin Rosenberg, Anders Kadziola, Joerg Daub and Mogens Brøndsted Nielsen

      Article first published online: 24 JUN 2015 | DOI: 10.1002/ejoc.201590051

      Thumbnail image of graphical abstract

      The cover picture shows that vinylheptafulvenes locked in a reactive conformation undergo ultrafast ring closure to dihydroazulenes – a rate enhancement by up to 950000 fold was observed relative to the ring closure of the unlocked molecule. In the article by S. L. Broman et al. on 4119 ff, the synthesis and studies of such molecules are presented. By incorporation of a triflate group, the system could be further functionalized using metal-catalyzed cross-coupling reactions. Attachment of sulfur end-capping groups was thereby achieved, which may allow for future anchoring of the molecule in molecular electronics junctions.

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

      Ubiquitous Benzoquinones, Multitalented Compounds for Palladium-Catalyzed Oxidative Reactions (pages 4053–4069)

      Alexandre Vasseur, Jacques Muzart and Jean Le Bras

      Article first published online: 30 MAR 2015 | DOI: 10.1002/ejoc.201500080

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      This review highlights the multifaceted properties of benzoquinone when it is involved in PdII-catalyzed oxidative reactions and presents mechanisms proposed in the literature.

  5. Short Communications

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

      Synthesis of Perfluoroalkyl-Substituted Vinylcyclopropanes by Way of Enhanced Neighboring Group Participation (pages 4071–4076)

      Christopher B. Kelly, Michael A. Mercadante, Emma R. Carnaghan, Matthew J. Doherty, Diana C. Fager, John J. Hauck, Allyson E. MacInnis, Leon J. Tilley and Nicholas E. Leadbeater

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500565

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      A diverse array of fluoroalkyl-substituted vinylcyclopropanes are prepared in a simple, high-yielding, two-step, one-pot protocol by means of cationic ring-closure.

    2. Anion Templation

      Sulfate Anion as a pH-Switchable Template: Three-State Switchable Systems Based on Diamidocarbazoles (pages 4077–4080)

      Krzysztof M. Bąk and Michał J. Chmielewski

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500546

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      The sulfate anion SO42– – one of the most versatile anionic templates – can be reversibly “switched off” in aprotic solvents by protonation to the very weakly binding HSO4 anion. This sharp ON/OFF behaviour opens new opportunities for switching and manipulation of supramolecular systems, as demonstrated here by the construction of two new acid/base switchable three-state systems.

    3. Asymmetric Alkynylation

      Enabling Asymmetric Alkynylation of Azaaryl Aldehydes with Soai Autocatalyst (pages 4081–4086)

      Matías Funes-Maldonado, Bora Sieng and Mohamed Amedjkouh

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500507

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      Amplification and propagation of asymmetry: Soai compound, generated by autocatalytic asymmetric amplification in up to 99.5 % ee, acts as a highly efficient catalyst for the ensuing asymmetric alkynylation of azaaryl aldehydes to produce alkynols with up to 86 % ee.

    4. Asymmetric Amplification

      Asymmetric Amplification Coupling Enantioselective Autocatalysis and Asymmetric Induction for Alkylation of Azaaryl Aldehydes (pages 4087–4092)

      Carlo Romagnoli, Bora Sieng and Mohamed Amedjkouh

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500508

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      Amplification and propagation of asymmetry: Soai autocatalyst is amplified in situ from 11 % to > 98 % ee and concomitantly catalyzes the addition of Zn(iPr)2 to azaaryl aldehydes to provide alkanols with up to 99 % ee. Also, exceptional amplifications of ee in one cycle are observed for both compounds.

    5. Photocatalysis

      Synthesis of β-Trifluoromethylated Ketones from Propargylic Alcohols by Visible Light Photoredox Catalysis (pages 4093–4097)

      Sehyun Park, Jung Min Joo and Eun Jin Cho

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500031

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      β-Trifluoromethyl ketones are synthesized from readily available propargylic alcohols by visible light photocatalysis. Trifluoromethylation followed by double-bond migration/keto-enol tautomerization provides β-trifluoromethyl ketones as the final product.

    6. Coumarin Functionalization

      A C-3-Selective Direct Alkylation of Coumarins by Using a Microwave-Assisted Xanthate-Based Radical Reaction (pages 4098–4101)

      Luis D. Miranda, Estefanía Icelo-Ávila, Ángel Rentería-Gómez, Michell Pila and Joaquín G. Marrero

      Article first published online: 2 JUN 2015 | DOI: 10.1002/ejoc.201500322

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      A vinylic and unactivated C–H bond of the coumarin system is replaced by an alkyl functionality trough a xanthate-based radical reaction (DLP = dilauroyl peroxide).

    7. Statin Synthesis

      A Practical Synthesis of Rosuvastatin and Other Statin Intermediates (pages 4102–4107)

      Stefano Tartaggia, Clark Ferrari, Marta Pontini and Ottorino De Lucchi

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500356

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      A new synthetic approach to statins has been developed. The efficient aldol condensation of heterocyclic aldehydes comprising the core structure of rosuvastatin and pitavastatin with a derivative of methyl 3-hydroxy-5-oxohexanoate affords products with the desired E geometry in high yield.

    8. Gold-Catalyzed 1,3-Transposition

      Gold(I)-Catalyzed 1,3-O-Transposition Reactions: Ynesulfonamides to Ynamides (pages 4108–4113)

      De-Yao Li, Yin Wei and Min Shi

      Article first published online: 2 JUN 2015 | DOI: 10.1002/ejoc.201500604

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      The gold-catalyzed 1,3-O-transposition reaction of ynesulfonamides provides a practical synthetic protocol for the synthesis of ynamides under mild conditions. This is the first 1,3-O-transposition example of ynesulfonamides in which a heteroatom is attached to the alkynyl terminal.

    9. Fluorination

      Synthesis of 5-Fluorotriazoles by Silver-Mediated Fluorination of 5-Iodotriazoles (pages 4114–4118)

      Damin Wang, Wenjing Sun and Taiwei Chu

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500338

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      A new strategy for the direct fluorination of 5-iodotriazoles with AgF and N1,N1,N2,N2-tetramethylethane-1,2-diamine (TMEDA) is described. Substrates with aliphatic or aromatic groups at the N1 position or 4-position can be converted to the corresponding fluorinated products in good to excellent yields. Preliminary mechanism studies were also performed.

  6. Full Papers

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

      Dihydroazulene/Vinylheptafulvene Photoswitch: Ultrafast Back Reaction Induced by Dihydronaphthalene Annulation (pages 4119–4130)

      Søren Lindbæk Broman, Oleg Kushnir, Martin Rosenberg, Anders Kadziola, Joerg Daub and Mogens Brøndsted Nielsen

      Article first published online: 7 MAY 2015 | DOI: 10.1002/ejoc.201500320

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      The switching rate for the DHA/VHF photoswitch has been changed from minutes to milliseconds by structural modification; locking the VHF in a reactive conformation, the rate of the back reaction (VHF [RIGHTWARDS ARROW] DHA) was increased by a factor of up to 950000. Also, sulfur anchoring groups were attached, possibly allowing the future exploitation of this fast photoswitch in molecular electronics.

    2. Organometallic Chemistry

      Double C–H Functionalization to Construct Polycyclic Heteroarenes Catalyzed by an Ionic Salt of a Pd Complex with an N-Heterocyclic Carbene Ligand (pages 4131–4142)

      Sanjay Kumar Ghosh, Bing-Chiuan Kuo, Hsiang-Yu Chen, Jia-Ying Li, Shuang-De Liu and Hon Man Lee

      Article first published online: 19 MAY 2015 | DOI: 10.1002/ejoc.201500417

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      The complex cis-[Pd(L)(PPh3)(H2O)2](SO3CF3)2, in which L is an amido-functionalized N-heterocyclic carbene (NHC) ligand, has been prepared. This complex was effective in catalyzing the double C–H functionalization of various nitrogen- and sulfur-containing heteroarenes to form fused polycyclic heteroaromatic compounds with alkynes in the presence of Cu(OAc)2 and tetra-n-butylammonium bromide.

    3. Mannich Reactions

      Mechanism Switch in Mannich-Type Reactions: ELF and NCI Topological Analyses of the Reaction between Nitrones and Lithium Enolates (pages 4143–4152)

      David Roca-López, Victor Polo, Tomás Tejero and Pedro Merino

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500447

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      Depending on the type of enolate the reaction mechanism changes from one-step to stepwise.

    4. Copper-Catalyzed Amination

      N-(1-Oxy-2-picolyl)oxalamic Acid as an Efficient Ligand for Copper-Catalyzed Amination of Aryl Iodides at Room Temperature (pages 4153–4161)

      Yongbin Wang, Jing Ling, Yu Zhang, Ao Zhang and Qizheng Yao

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500279

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      N-(1-Oxy-2-picolyl)oxalamic acid was identified as an efficient ligand for promoting Cu-catalyzed amination of aryl halides with aliphatic amines and ammonia at room temperature.

    5. Thioethers

      One-Pot Copper-Catalysed Thioetherification of Aryl Halides Using Alcohols and Lawesson's Reagent in Diglyme (pages 4162–4167)

      Mohammad Gholinejad

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500256

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      A copper-catalysed method for the thioetherification of alcohols with aryl halides using Lawesson's reagent was developed.

    6. Diastereoselective Addition

      Diastereoselective Construction of 3-Aminooxindoles with Adjacent Stereocenters: Stereocontrolled Addition of γ-Substituted Allylindiums to Isatin Ketimines (pages 4168–4189)

      Nayyar Ahmad Aslam, Srinivasarao Arulananda Babu, Soniya Rani, Shivam Mahajan, Jagmohan Solanki, Makoto Yasuda and Akio Baba

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500340

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      A synthetic protocol for the diastereoselective indium-mediated Barbier-type C–C bond formation has been developed. The addition of γ-substituted allylic reagents to the C=N bond of isatin ketimines was employed for the synthesis of several new 3-aminooxindoles that have two contiguous stereocenters.

    7. Medium-Ring Heterocycles

      Gold- and Silver-Catalyzed 7-endo-dig Cyclizations for the Synthesis of Oxazepines (pages 4190–4197)

      Anatoly A. Peshkov, Anton A. Nechaev, Olga P. Pereshivko, Jan L. Goeman, Johan Van der Eycken, Vsevolod A. Peshkov and Erik V. Van der Eycken

      Article first published online: 22 MAY 2015 | DOI: 10.1002/ejoc.201500357

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      A comprehensive study on gold- and silver-catalyzed cycloisomerizations of hydroxypropargylamides into oxazepines is described.

    8. Natural Product Synthesis

      Synthesis and Biological Evaluation of Dichlorinated Chondramide Derivatives (pages 4198–4213)

      Dominic Becker and Uli Kazmaier

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500369

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      Investigation of the methyl-substitution pattern in the polyketide fragment of new ethyl-substituted dichlorinated chondramides.

    9. Azonia Aromatic Cations

      Azonia Aromatic Cations by Ring-Closing Metathesis: Synthesis of Azaquinolizinium Cations (pages 4214–4223)

      Alberto Abengózar, Beatriz Abarca, Ana M. Cuadro, David Sucunza, Julio Álvarez-Builla and Juan J. Vaquero

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500404

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      A new approach for the synthesis of the 1-azaquinolizinium (pyrimido[1,2-a]pyrimidin-5-ium) heterocycle and some simple derivatives is described. This strategy, based on an unprecedented ring-closing metathesis (RCM) reaction to construct the pyrimidinium ring, was also applied to the first reported synthesis for the benzo-1-azaquinolizinium (pyrimido[2,1-a]isoquinolinium) cation.

    10. Porphyrinoids

      Synthesis of Functionalized BODIPYs, BODIPY-Corrole, and BODIPY-Porphyrin Arrays with 1,2,3-Triazole Linkers Using the 4-Azido(tetrafluorophenyl)-BODIPY Building Block (pages 4224–4237)

      Hartwig R. A. Golf, Anna M. Oltmanns, Duc H. Trieu, Hans-Ulrich Reissig and Arno Wiehe

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500413

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      The synthesis of meso-functionalized BODIPYs using the copper(I)-catalyzed cycloaddition of terminal alkynes with an azido-substituted BODIPY is presented. The scope of this reaction was extended to the synthesis of OH- and SF5-substituted BODIPY-CuIII-corrole and BODIPY-ZnII-porphyrin arrays, demonstrating a versatile approach towards multichromophoric systems.

    11. Multicomponent Reactions

      Iron-Catalysed Oxidative Ugi-Type Multicomponent Reaction Using (Arylmethyl)amines as Imine Precursors (pages 4238–4245)

      Shashikant U. Dighe, Shivalinga Kolle and Sanjay Batra

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500464

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      The oxidative three-component Ugi reaction catalysed by Fe(NO3)3·9H2O using (arylmethyl)amine as the imine source under aerobic conditions is described.

    12. Total Synthesis

      Total Synthesis of Myrmekioside A, a Mono-O-alkyl-diglycosylglycerol from Marine Sponge Myrmekioderma sp. (pages 4246–4253)

      Jun Zhang, Chunxia Li, Linlin Sun, Guangli Yu and Huashi Guan

      Article first published online: 28 MAY 2015 | DOI: 10.1002/ejoc.201500471

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      Myrmekioside A, a natural mono-O-alkyl-diglycosylglycerol from a marine sponge, was synthesized for the first time. The β-glycosidic linkages were constructed by the neighbouring-group-participation approach. This synthetic approach may be applicable to other natural mono-O-alkyl-diglycosylglycerols and their structural variants.

    13. Tandem Cyclization

      A Cascade Approach to Naphthalene Derivatives from o-Alkynylbenzaldehydes and Enolizable Ketones via in-situ-Formed Acetals (pages 4254–4260)

      Seetharaman Manojveer and Rengarajan Balamurugan

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500497

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      In situ acetal formation assists the intermolecular cyclization of o-alkynyl aryl aldehydes with enolizable ketones to give diverse naphthyl ketone derivatives under metal-free catalytic conditions.

    14. Domino Reactions

      Intra-Intermolecular Palladium-Catalyzed Domino Reactions of Glycine Allylamides for the Synthesis of Diversely Functionalized Piperazinones (pages 4261–4268)

      Gianluigi Broggini, Egle M. Beccalli, Tea Borelli, Filippo Brusa, Silvia Gazzola and Alberto Mazza

      Article first published online: 27 MAY 2015 | DOI: 10.1002/ejoc.201500386

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      Inter-intramolecular domino palladium-catalyzed reactions of N-tosylglycine allylamides were used to access piperazinones with functional groups that can undergo further transformations. Aminochlorination and aminoacetoxylation processes were achieved by using CuCl2 and PhI(OAc)2 as oxidizing agents to give 5-chloromethyl- and 5-acetoxymethyl-substituted piperazinones, respectively.

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