European Journal of Organic Chemistry

Cover image for Vol. 2015 Issue 25

September 2015

Volume 2015, Issue 25

Pages 5471–5671

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    8. Correction
    1. Thiourea-Bridged Nanodiamond Glycoconjugates as Inhibitors of Bacterial Adhesion (Eur. J. Org. Chem. 25/2015)

      Claudia Fessele, Stefan Wachtler, Vijayanand Chandrasekaran, Carina Stiller, Thisbe K. Lindhorst and Anke Krueger

      Article first published online: 19 AUG 2015 | DOI: 10.1002/ejoc.201590070

      Thumbnail image of graphical abstract

      The cover picture shows glyconanodiamond where the sugars are immobilized onto the diamond by thiourea bridging. This novel ligation technique for the functionalization of nanodiamond enables the grafting of different types of saccharide motifs. These glycoconjugates can be used to probe the carbohydrate-specific interaction of bacteria and furthermore to inhibit biofilm formation. The article also reports on the quantification of bacterial adhesion to different glyconanodiamond conjugates by employing a tailor-made sandwich assay. Details are discussed in the article by T. K. Lindhorst, A. Krueger et al. on 5519 ff.

  2. Graphical Abstract

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

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

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    8. Correction
    1. Unique Lewis Acid Catalysis

      Hafnium Trifluoromethanesulfonate [Hf(OTf)4] as a Unique Lewis Acid in Organic Synthesis (pages 5485–5499)

      Haruro Ishitani, Hirotsugu Suzuki, Yuki Saito, Yasuhiro Yamashita and Shū Kobayashi

      Article first published online: 2 JUN 2015 | DOI: 10.1002/ejoc.201500423

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      This microreview summarizes examples of Hf(OTf)4-mediated or -catalyzed organic reactions. Hafnium triflate shows outstanding performance in catalytic Friedel–Crafts acylation reactions and in Mannich-type reactions of imines, hydrazones, and N,O-acetals.

  5. Short Communications

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    8. Correction
    1. One-Pot C–H Iodination

      Facile, One-Pot, and Gram-Scale Synthesis of 3,4,5-Triiodoanisole through a C–H Iodination/ipso-Iododecarboxylation Strategy: Potential Application towards 3,4,5-Trisubstituted Anisoles (pages 5501–5508)

      Raed M. Al-Zoubi, Hussein Al-Mughaid, Mariam A. Al-Zoubi, Khaled T. Jaradat and Robert McDonald

      Article first published online: 6 AUG 2015 | DOI: 10.1002/ejoc.201500887

      Thumbnail image of graphical abstract

      The facile and efficient synthesis of hitherto unknown 3,4,5-triiodoanisole in a tandem one-pot C–H iodination/ipso-iododecarboxylation reaction that is catalytic, scalable, easy to work up, and easy to purify is disclosed. Potential application of the target compound as a precursor for novel site-selective metal–iodine exchange and Suzuki–Miyaura cross-coupling reactions are demonstrated.

    2. Water-Soluble Phosphanes

      Tetrasulfonated 1,2-Bis(diphenylphosphanyl)ethane as a Building Block for the Synthesis of Disulfonated Alkyldiphenylphosphanes (pages 5509–5512)

      Julien Denis, Michel Ferreira, Hervé Bricout, Cécile Machut, Sébastien Tilloy and Eric Monflier

      Article first published online: 24 JUL 2015 | DOI: 10.1002/ejoc.201500772

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      A new methodology for the synthesis of disulfonated alkyldiphenylphosphanes bearing an oleum-sensitive group has been developed. Alkylation of 1,2-bis(diphenylphosphanyl)ethane (DPPETS) followed by cleavage gives the desired disulfonated alkyldiphenylphosphane products.

    3. Iron-Catalyzed Aromatization

      Fe(OTf)3-Catalyzed Aromatization of Substituted 3-Methyleneindoline and Benzo­furan Derivatives: A Selective Route to C-3-Alkylated Indoles and Benzofurans (pages 5513–5517)

      Sandip Kundal, Swapnadeep Jalal, Kartick Paul and Umasish Jana

      Article first published online: 27 JUL 2015 | DOI: 10.1002/ejoc.201500540

      Thumbnail image of graphical abstract

      A simple selective synthesis of 3-substituted indoles and benzofurans by isomerization of 3-methyleneindoline and benzofuran derivatives with Fe(OTf)3 was developed. The substrates were obtained by the domino Heck–Suzuki coupling of 2-bromo-N-propargylamide or 2-bromopropargyl ether. The method features high yields, mild reaction conditions, wide functional group tolerance, and an environmentally friendly catalyst.

  6. Full Papers

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

      Thiourea-Bridged Nanodiamond Glycoconjugates as Inhibitors of Bacterial Adhesion (pages 5519–5525)

      Claudia Fessele, Stefan Wachtler, Vijayanand Chandrasekaran, Carina Stiller, Thisbe K. Lindhorst and Anke Krueger

      Article first published online: 29 JUN 2015 | DOI: 10.1002/ejoc.201500532

      Thumbnail image of graphical abstract

      Thiourea-bridging is a new approach to conjugating nanodiamond nanoparticles and biomolecules. This was exemplified by preparation of saccharide-functionalized nanodiamonds (NDs) that were characterized and employed in biological studies. These studies revealed specific ND binding to E. coli bacterial cells.

    2. Iron Catalysis

      Synthesis of (R)-BINOL-Derived (Cyclopentadienone)iron Complexes and Their Application in the Catalytic Asymmetric Hydrogenation of Ketones (pages 5526–5536)

      Piotr Gajewski, Marc Renom-Carrasco, Sofia Vailati Facchini, Luca Pignataro, Laurent Lefort, Johannes G. de Vries, Raffaella Ferraccioli, Umberto Piarulli and Cesare Gennari

      Article first published online: 23 JUL 2015 | DOI: 10.1002/ejoc.201500796

      Thumbnail image of graphical abstract

      A family of chiral (cyclopentadienone)iron complexes with an (R)-BINOL-derived backbone is described. The complexes differ in the substituents at the 3,3′-positions of the binaphthyl residue (H, OH, OR, OCOR, or OSO2R) or at the 2,5-positions of the cyclopentadienone ring (trimethylsilyl, or Ph) and provide up to 77 % ee in the asymmetric hydrogenation of ketones.

    3. Dye-Sensitized Solar Cells

      Fluoren-9-ylidene-Based Dyes for Dye-Sensitized Solar Cells (pages 5537–5545)

      Alexis Tigreros, Danisha M. Rivera-Nazario, Alejandro Ortiz, Nazario Martin, Braulio Insuasty and Luis A. Echegoyen

      Article first published online: 24 JUL 2015 | DOI: 10.1002/ejoc.201500602

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      Three dyes with hindered fluoren-9-ylidene hydrophobic groups as antennas are synthesized, and their electrochemical, photophysical, and photovoltaic properties are evaluated. As the starburst shape of the dyes increases, the open-cell voltage (VOC) increases from 0.79 to 0.83 V, which leads to an increase of 18 % in the power-conversion efficiency (PCE).

    4. Decarbonylative Cross-Coupling

      Nickel-Catalyzed Decarbonylative Cou­pling of Aryl Esters and Arylboronic Acids (pages 5546–5553)

      Nicole A. LaBerge and Jennifer A. Love

      Article first published online: 24 JUL 2015 | DOI: 10.1002/ejoc.201500630

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      Functionalized bis(hetero)aryl motifs are easily accessed from heteroaryl esters and boronic acids by using decarbonylative coupling. The Suzuki–Miyaura-type cross-coupling is catalyzed by an affordable low-toxic catalyst system composed of Ni(cod)2 and PCy3. This methodology presents an attractive alternative to the use of palladium catalysts currently used in industry to acquire bis(hetero)aryls.

    5. Fluorinated Sulfoxides

      Circular Dichroism and TDDFT Investigation of Chiral Fluorinated Aryl Benzyl Sulfoxides (pages 5554–5562)

      Roberto Berardozzi, Ciro A. Guido, Maria Annunziata M. Capozzi, Cosimo Cardellicchio, Lorenzo Di Bari and Gennaro Pescitelli

      Article first published online: 28 JUL 2015 | DOI: 10.1002/ejoc.201500648

      Thumbnail image of graphical abstract

      A series of ten chiral aryl benzyl sulfoxides with perfluorinated aromatic rings has been investigated by means of electronic circular dichroism and time-dependent DFT calculations. The perfluorination has a large impact on the molecular orbitals and electronic transitions. Range-separated functionals perform much better than global hybrids in the prediction of the ECD spectra.

    6. Near-Infrared Probes

      Near-Infrared Fluorescent 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacene Probes for One- and Two-Photon Fluorescence Bio­imaging (pages 5563–5571)

      Bosung Kim, Xiling Yue, Binglin Sui, Xinfu Zhang, Yi Xiao, Mykhailo V. Bondar, Junko Sawada, Masanobu Komatsu and Kevin D. Belfield

      Article first published online: 23 JUL 2015 | DOI: 10.1002/ejoc.201500664

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      Two new BODIPY-based near-IR emitting fluorescent dyes were investigated that have a high lysosomal selectivity and – when incorporated in silica nanoparticles surface-functionalized with the RGD peptide – afford thick-tissue vascular imaging.

    7. Sugar Amino Acids

      Synthesis of Building Blocks for Carbopeptoids and Their Triazole Isoster Assembly (pages 5572–5584)

      Vitālijs Rjabovs, Pāvels Ostrovskis, Daniels Posevins, Gļebs Kiseļovs, Viktors Kumpiņš, Anatoly Mishnev and Māris Turks

      Article first published online: 23 JUL 2015 | DOI: 10.1002/ejoc.201500695

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      Syntheses of new γ- and δ-furanoid sugar amino acids have been accomplished. The obtained N-protected building blocks are suitable for chain elongation, as was verified by the synthesis of tetrameric carbopeptoids.

    8. Chalcogen-Nitrogen Heterocycles

      [1,2,5]Selenadiazolo[3,4-b]pyrazines: Synthesis from 3,4-Diamino-1,2,5-selena­diazole and Generation of Persistent Radical Anions (pages 5585–5593)

      Lidia S. Konstantinova, Irina E. Bobkova, Yulia V. Nelyubina, Elena A. Chulanova, Irina G. Irtegova, Nadezhda V. Vasilieva, Paula S. Camacho, Sharon E. Ashbrook, Guoxiong Hua, Alexandra M. Z. Slawin, J. Derek Woollins, Andrey V. Zibarev and Oleg A. Rakitin

      Article first published online: 23 JUL 2015 | DOI: 10.1002/ejoc.201500742

      Thumbnail image of graphical abstract

      3,4-Diamino-1,2,5-selenadiazole was synthesized and used for preparing novel [1,2,5]selenadiazolo[3,4-b]pyrazines. Electrochemical reduction of the latter into persistent radical anions (RAs) was studied by CV and the RAs were characterized by EPR combined with DFT calculations.

    9. Iron-Catalyzed Dealkylation

      Iron-Catalyzed Acylative Dealkylation of N-Alkylsulfoximines (pages 5594–5602)

      Philip Lamers, Daniel L. Priebbenow and Carsten Bolm

      Article first published online: 30 JUL 2015 | DOI: 10.1002/ejoc.201500855

      Thumbnail image of graphical abstract

      The dealkylation of N-alkylsulfoximines has been developed utilizing TBHP as oxidant and a catalytic amount of iron chloride to furnish a range of N-acyl- and N-aroylsulfoximines. This method facilitates the use of N-alkyl protecting groups that provide very stable N-protected sulfoximine derivatives that can be readily modified at sites other than the nitrogen atom.

    10. Dipeptide Ureas

      A One-Pot Synthesis of Symmetrical and Unsymmetrical Dipeptide Ureas (pages 5603–5609)

      Antoine Abou Fayad, Cristina Pubill-Ulldemolins, Sunil V. Sharma, David Day and Rebecca J. M. Goss

      Article first published online: 30 JUL 2015 | DOI: 10.1002/ejoc.201500589

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      We describe a flexible and high yielding synthesis of 1,3-disubstituted ureas, that allows for the construction of both symmetrical and unsymmetrical dipeptide ureas, including easy access to 13C labelled ureas, from amino acids and carbon dioxide at atmospheric pressure.

    11. Porphyrinoids

      Insights into the Synthesis and the Solution Behavior of meso-Aryloxy- and Alkoxy-Substituted Porphyrins (pages 5610–5619)

      Kirill P. Birin, Yulia G. Gorbunova, Aslan Yu. Tsivadze, Alla G. Bessmertnykh-Lemeune and Roger Guilard

      Article first published online: 28 JUL 2015 | DOI: 10.1002/ejoc.201500628

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      Synthetic approaches to meso-RO-porphyrins were investigated. Mono- and di-RO-substituted porphyrins were synthesized from 5,15-dibromoporphyrins by using an SNAr reaction. Furthermore, unsymmetrical porphyrinyl alkyl ethers were prepared from NiII 5-bromo-15-RO-porphyrin by using Pd-catalyzed coupling reactions. Concentration-dependent aggregation of ZnII meso-RO-porphyrins was studied by NMR spectroscopy.

    12. Chemoenzymatic Synthesis

      Total Synthesis of Solandelactones A and B (pages 5620–5632)

      Nils C. Eichenauer, Anja C. M. Nordschild, Martina Bischop, Dominik Schumacher, Marcel K. W. Mackwitz, Roxanne Tschersich, Thorsten Wilhelm and Jörg Pietruszka

      Article first published online: 30 JUL 2015 | DOI: 10.1002/ejoc.201500700

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      During efforts focusing on the efficient synthesis of key building blocks leading to marine natural product oxylipins, the synthesis of the title compounds was ultimately achieved. Noteworthy in the approach taken is the short and efficient chemoenzymatic sequence affording the cyclopropyl lactone unit.

    13. Library Synthesis

      Synthesis of (Arylamido)pyrrolidinone Libraries through Ritter-Type Cascade Reactions of Dihydroxylactams (pages 5633–5639)

      Peng Wu, Michael Åxman Petersen, Rico Petersen, Martin Ohsten Rasmussen, Karine Bonnet, Thomas E. Nielsen and Mads H. Clausen

      Article first published online: 30 JUL 2015 | DOI: 10.1002/ejoc.201500712

      Thumbnail image of graphical abstract

      Ritter-type reactions of arylnitriles and in-situ-generated N-acyliminium ions gave tetrahydropyrrolo[2,3-d]oxazol-5-ones in excellent yields. A subsequent acidic hydrolysis yielded new (arylamido)pyrrolidinones with excellent cis diastereoselectivity. A combined Ritter–hydrolysis cascade procedure was successfully used for the construction of a screening library containing 706 molecules.

    14. Nitrogen Heterocycles

      Synthesis of 3-Organoseleno-Substituted Quinolines through Cyclization of 2-­Amino­phenylprop-1-yn-3-ols Promoted by Iron(III) Chloride with Diorganyl Diselenides (pages 5640–5648)

      André Luiz Stein, Alisson Rodrigues Rosário and Gilson Zeni

      Article first published online: 30 JUL 2015 | DOI: 10.1002/ejoc.201500766

      Thumbnail image of graphical abstract

      We have described the application of iron(III) chloride and diorganyl diselenides as cooperative partners in the cyclization of (2-aminoaryl)-2-ynols for the regioselective synthesis of 3-organoseleno quinolines.

    15. Organocatalysis

      Prolinamide-Derived Ionic-Liquid-Supported Organocatalyst for Asymmetric Mono- and Bis-Aldol Reactions in the Presence of Water (pages 5649–5654)

      Aleksander S. Kucherenko, Vasiliy V. Gerasimchuk, Vladislav G. Lisnyak, Yulia V. Nelyubina and Sergei G. Zlotin

      Article first published online: 30 JUL 2015 | DOI: 10.1002/ejoc.201500775

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      A recyclable prolinamide-derived ionic-liquid-supported organocatalyst bearing an auxiliary Brønsted-acidic group has been developed. It catalyzes asymmetric mono- and bis-aldol reactions of aromatic aldehydes with cyclic or linear ketones in aqueous medium and retains excellent catalytic performance (up to 96:4 dr and 81–99 % ee) over ten cycles.

    16. Carbazole Synthesis

      Gram Scale Total Synthesis of 2-Hydroxy-3-methylcarbazole, Pyrano[3,2-a]carbazole and Prenylcarbazole Alkaloids (pages 5655–5662)

      Jianxin Dai, Dengke Ma, Chunling Fu and Shengming Ma

      Article first published online: 27 JUL 2015 | DOI: 10.1002/ejoc.201500783

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      Carbazole alkaloid natural products including 2-hydroxy-3-methylcarbazole, girinimbine, murrayacine, mukoenine-A, and heptaphylline have been produced on gram scale. Girinimbine and murrayacine were synthesized using PhB(OH)2-mediated intermolecular cyclization with 3-methylbut-2-enal whereas mukoenine-A and heptaphylline were best accessed using a Pd-catalyzed allylation/Claisen rearrangement.

    17. Alkyne-Azide Cycloaddition

      Metal-Free Intramolecular Alkyne-Azide Cycloaddition To Construct the Pyraz­olo[4,3-f][1,2,3]triazolo[5,1-c][1,4]oxazepine Ring System (pages 5663–5670)

      Eglė Arbačiauskienė, Vaida Laukaitytė, Wolfgang Holzer and Algirdas Šačkus

      Article first published online: 28 JUL 2015 | DOI: 10.1002/ejoc.201500541

      Thumbnail image of graphical abstract

      A new pyrazolo[4,3-f][1,2,3]triazolo[5,1-c][1,4]oxazepine ring system was synthesized by employing a metal-free, intramolecular alkyne-azide cycloaddition reaction that uses readily available starting materials.

  7. Correction

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    8. Correction
    1. You have free access to this content
      Synthetic Approaches to Anti-Inflammatory Macrolactones of the Oxacyclodo­decindione Type (page 5671)

      Johannes Tauber, Kristina Rudolph, Markus Rohr, Gerhard Erkel and Till Opatz

      Article first published online: 24 JUL 2015 | DOI: 10.1002/ejoc.201500930

      This article corrects:

      Synthetic Approaches to Anti-Inflammatory Macrolactones of the Oxacyclododecindione Type

      Vol. 2015, Issue 16, 3587–3608, Article first published online: 21 APR 2015

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