European Journal of Organic Chemistry

Cover image for Vol. 2014 Issue 31

November 2014

Volume 2014, Issue 31

Pages 6809–7048

  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
      Six Peroxide Groups in One Molecule – Synthesis of Nine-Membered Bicyclic Silyl Peroxides (Eur. J. Org. Chem. 31/2014)

      Ashot V. Arzumanyan, Alexander O. Terent'ev, Roman A. Novikov, Valentin G. Lakhtin, Vladimir V. Chernyshev, Andrew N. Fitch and Gennady I. Nikishin

      Article first published online: 24 OCT 2014 | DOI: 10.1002/ejoc.201490087

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      The cover picture shows extremely explosive compounds containing two nine-membered Si-peroxide rings bridged by an ethane, ethene, or ethyne group. These peroxides were synthesized by the reaction of 1,2-bis[dichloro(alkyl)silyl]ethanes, (E)-1,2-bis[dichloro(methyl)silyl]ethene, or 1,2-bis[dichloro(methyl)silyl]ethyne with 1,1′-dihydroperoxyperoxides and were isolated as individual compounds. Details are discussed in the article by A. Terent'ev et al. on p. 6877 ff.

  2. Graphical Abstract

    1. Top of page
    2. Cover Picture
    3. Graphical Abstract
    4. News
    5. Microreview
    6. Short Communications
    7. Full Papers
    1. Graphical Abstract: Eur. J. Org. Chem. 31/2014 (pages 6809–6817)

      Article first published online: 24 OCT 2014 | DOI: 10.1002/ejoc.201490089

  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. Hydroamination

      Efficient Anti-Markovnikov-Selective Catalysts for Intermolecular Alkyne Hydroamination: Recent Advances and Synthetic Applications (pages 6825–6840)

      Jacky C. -H. Yim and Laurel L. Schafer

      Article first published online: 28 JUL 2014 | DOI: 10.1002/ejoc.201402300

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      Hydroamination, the catalytic addition of an N–H bond across a C–C unsaturation site, is a 100 % atom-economical route for the construction of nitrogen-containing small molecules. However, regioselectivity is a great challenge for this reaction. This Microreview focuses on recent advances and highlights some synthetic applications of anti-Markovnikov-selective intermolecular alkyne hydroamination.

  5. Short Communications

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

      Synthesis and Glycoconjugation of an Azido-BF2–Azadipyrromethene Near-Infrared Fluorochrome (pages 6841–6845)

      Dan Wu, Shane Cheung, Robin Daly, Helen Burke, Eoin M. Scanlan and Donal F. O'Shea

      Article first published online: 2 OCT 2014 | DOI: 10.1002/ejoc.201402960

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      The synthesis of a water-soluble azido near-IR fluorochrome based on the BF2–azadipyrromethene fluorophore class is described. The fluorochrome can be effectively conjugated to alkyne-substituted carbohydrates by click chemistry in water at room temperature in 20 min. This azido-BF2–azadipyrromethene fluorochrome offers the potential to be a new near-IR imaging research tool for biology.

    2. C–P Bond Formation

      Carbon–Phosphorus Bond Formation by Enantioselective Palladium-Catalyzed Allylation of Diphenylphosphine Oxide (pages 6846–6849)

      Liang Zhang, Wei Liu and Xiaoming Zhao

      Article first published online: 30 SEP 2014 | DOI: 10.1002/ejoc.201403024

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      The Pd-catalyzed asymmetric allylation of diphenylphosphine oxide to form P-allylated products in yields up to 95 % with 97 % ee is described. Pd-catalyzed allylation of (E)-methyl allyl carbonates with diisopropyl phosphonate is accomplished, which regioselectively gives linear P-allylated products in 65–95 % yields; BINAP = 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl.

    3. Oxidative Coupling

      Copper-Catalyzed Formation of C–O Bonds by Oxidative Coupling of Benzylic Alcohols with Ethers (pages 6850–6853)

      Quan Wang, Haoran Geng, Wen Chai, Xiaojun Zeng, Min Xu, Cheng Zhu, Renzhong Fu and Rongxin Yuan

      Article first published online: 29 SEP 2014 | DOI: 10.1002/ejoc.201402885

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      The copper-catalyzed formation of C–O bonds by oxidative coupling of benzylic alcohols with ethers is realized in open air. A series of α-acyloxy ethers were obtained in good yields with aqueous tert-butyl hydroperoxide as the oxidant.

    4. Arylation

      Cesium Carbonate Promoted Direct Arylation of Hydroxylamines and Oximes with Diaryliodonium Salts (pages 6854–6857)

      Yang Yang, Xunshen Wu, Jianwei Han, Song Mao, Xiaofei Qian and Limin Wang

      Article first published online: 24 SEP 2014 | DOI: 10.1002/ejoc.201402920

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      An efficient method for the transition-metal-free arylation of hydroxylamines and oximes with diaryliodonium salts is described. A range of N-arylhydroxylamines with various aryl substituents that would be useful in the preparation of valuable chemicals are obtained in good to excellent yields. Cbz = benzyloxycarbonyl, Boc = tert-butoxycarbonyl, TBDMS = tert-butyldimethylsilyl, TBDPS = tert-butyldiphenylsilyl, Bn = benzyl, Tf = trifluoromethylsulfonyl.

    5. Domino Reactions

      Synthesis of 2-Alkylideneisochromans by Cyclocarbonylative Sonogashira Reactions (pages 6858–6862)

      Laura Antonella Aronica, Luca Giannotti, Stefano Giuntini and Anna Maria Caporusso

      Article first published online: 24 SEP 2014 | DOI: 10.1002/ejoc.201402979

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      An atom-economic, palladium-catalyzed carbonylative Sonogashira reaction/cyclisation sequence is used for the preparation of 2-alkylideneisochromans in high yields with high stereoselectivity.

    6. Alkenylation

      Ruthenium-Catalyzed Switchable N–H/C–H Alkenylation of 6-Phenyl(dihydro)pyridazinones with Alkynes (pages 6863–6867)

      Wei Wang, Lei Liang, Fengrong Xu, Wenjie Huang, Yan Niu, Qi Sun and Ping Xu

      Article first published online: 25 SEP 2014 | DOI: 10.1002/ejoc.201402986

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      A Ru-catalyzed switchable N–H/C–H alkenylation reaction of 6-phenyl(dihydro)pyridazin-3(2H)-ones triggered by a N2/O2 atmosphere is developed. To achieve switchable modification of the two important sites of the widely used pharmacophore, a simple and efficient procedure is utilized that affords excellent activity, high selectivity, and good tolerance of a wide range of functional groups.

    7. Cooperative Catalysis

      Brønsted Acid/Lewis Acid Cooperatively Catalyzed Addition of Diazoesters to 2H-Chromene Acetals (pages 6868–6872)

      Yi Luan, Yue Qi, Hongyi Gao, Qianqian Ma and Scott E. Schaus

      Article first published online: 25 SEP 2014 | DOI: 10.1002/ejoc.201403043

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      A Brønsted acid/Lewis acid dual catalyst system is developed to promote efficient C–C bond formation between oxocarbenium precursors derived from chromene acetals and ethyl diazoacetate. The reaction proceeds under mild conditions and is tolerant of functionalized 2H-chromenes and isochromene acetals. An asymmetric variant of diazoacetate addition towards 2H-chromene acetals is also described.

    8. Organocatalysis

      First Microwave-Assisted Catalytic Wittig Reaction (pages 6873–6876)

      Thomas Werner, Marcel Hoffmann and Sunetra Deshmukh

      Article first published online: 24 SEP 2014 | DOI: 10.1002/ejoc.201403113

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      The first catalytic Wittig reaction under microwave irradiation is reported. Readily available tributylphosphine oxide acts as the precatalyst. Under optimized conditions, a variety of aromatic, aliphatic, and heteroaromatic aldehydes could be converted efficiently. Moreover, one example of the first asymmetric version under these conditions is enclosed.

  6. Full Papers

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

      Six Peroxide Groups in One Molecule – Synthesis of Nine-Membered Bicyclic Silyl Peroxides (pages 6877–6883)

      Ashot V. Arzumanyan, Alexander O. Terent'ev, Roman A. Novikov, Valentin G. Lakhtin, Vladimir V. Chernyshev, Andrew N. Fitch and Gennady I. Nikishin

      Article first published online: 4 SEP 2014 | DOI: 10.1002/ejoc.201402895

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      Compounds containing two nine-membered peroxide rings bridged by an ethane, ethene, or ethyne group are synthesized. Each ring is formed by the replacement of two geminal chlorine atoms at the silicon atom with the hydroperoxide groups of one peroxide molecule. The peroxides are isolated by crystallization or silica gel filtration; unexpectedly, all of these compounds are extremely explosive.

    2. Fluorinated Oligoporphyrins

      Synthesis of Highly Fluoroalkyl-Functionalized Oligoporphyrin Systems (pages 6884–6895)

      Lukas Felix, Ugur Sezer, Markus Arndt and Marcel Mayor

      Article first published online: 12 SEP 2014 | DOI: 10.1002/ejoc.201402816

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      Massive but volatile molecules have been obtained by functionalizing the periphery of oligoporphyrins with highly fluorinated alkyl chains. The statistical nature of the reaction gives libraries consisting of molecules with well-defined masses but small structural diversity. Laser desorption and post-ionization studies demonstrated the potential of these libraries as sources of heavy particles.

    3. Base-Initiated Rearrangement

      Synthesis of 1,2-Diols and Their Base-Initiated Rearrangement to Butyrolactones (pages 6896–6902)

      Mauro Moliterno, Cristiana Margarita, Silvia Panarello, Riccardo Salvio and Marco Bella

      Article first published online: 17 SEP 2014 | DOI: 10.1002/ejoc.201402853

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      Unsaturated 3-hydroxybutyrolactones (isotetronic acids) have been prepared by a novel rearrangement of 1,2-diols involving an unusual alkyl shift. A possible mechanism is described with the aid of DFT calculations.

    4. Amino-Substituted Carbasugars

      Synthesis and α-Glucosidase and α-Amylase Inhibitory Activity Evaluation of Azido- and Aminocyclitols (pages 6903–6917)

      Gökay Aydin, Khamis Ally, Fatih Aktaş, Ertan Şahin, Arif Baran and Metin Balci

      Article first published online: 22 SEP 2014 | DOI: 10.1002/ejoc.201402762

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      Aminocyclitols are found in many natural products with remarkable biological activities. The synthesis of various amino-substituted carbasugars and their inhibitory effects against α-glucosidase and α-amylase are discussed.

    5. Reaction Mechanisms

      Addition–Elimination versus Direct Substitution Mechanisms for Arene Chlorination (pages 6918–6924)

      Boris Galabov, Gergana Koleva, Jing Kong, Henry F. Schaefer III and Paul v. R. Schleyer

      Article first published online: 15 SEP 2014 | DOI: 10.1002/ejoc.201402765

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      The present comprehensive DFT computational exploration of aromatic chlorination predicts that the barriers for the addition of Cl2 to benzene, toluene and naphthalene catalyzed by HCl in the gas phase and in simulated CCl4 solution can be even lower than the barriers for direct substitution. Moreover, substitution products also can arise from stepwise Cl2 addition/HCl elimination routes.

    6. Supramolecular Chemistry

      1,8-Dioxyanthracene-Derived Crown Ethers: Synthesis, Complexation with Paraquat and Assembly of a Tetracationic Cyclophane-Crown Ether Based [2]Catenane (pages 6925–6934)

      Bo Tang, Hong-Mei Yang, Wen-Jing Hu, Ming-Liang Ma, Yahu A. Liu, Jiu-Sheng Li, Biao Jiang and Ke Wen

      Article first published online: 19 SEP 2014 | DOI: 10.1002/ejoc.201402876

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      Sandwich and crescent conformations were adopted by bis-1,8-dioxyanthracene-based crown ethers upon complexation with methyl viologen dication (see Scheme). The structure of the complexes are highly dependent on the length of polyether chains of the crown ethers.

    7. Asymmetric Sulfinylation

      DMAP-Catalysed Sulfinylation of Diacetone-D-Glucose: Improved Method for the Synthesis of Enantiopure tert-Butyl Sulfoxides and tert-Butanesulfinamides (pages 6935–6944)

      Ahmed Chelouan, Rocío Recio, Ana Alcudia, Noureddine Khiar and Inmaculada Fernández

      Article first published online: 16 SEP 2014 | DOI: 10.1002/ejoc.201402673

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      An improved method for the tert-butanesulfinylation of diacetone glucose with tert-butanesulfinyl chloride is reported. The resulting (RS)-DAG sulfinate ester 2RS is an excellent C- and N-sulfinylating agent that can be used for the synthesis of relevant enantiopure sulfoxides and (SS)-tert-butanesulfinamides.

    8. Selenium Heterocycles

      Synthesis of 2-Substituted 1,3-Benzoselenazoles from Carboxylic Acids Promoted by Tributylphosphine (pages 6945–6952)

      Cátia Schwartz Radatz, Daniel S. Rampon, Renata A. Balaguez, Diego Alves and Paulo Henrique Schneider

      Article first published online: 22 SEP 2014 | DOI: 10.1002/ejoc.201402808

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      A metal-free synthesis of 2-substituted 1,3-benzoselenazoles by the reaction of bis(2-aminophenyl)diselenide with carboxylic acids, promoted by tributylphosphine is reported. For the first time, 2-alkyl-1,3-benzoselenazoles could be obtained from aliphatic carboxylic acids and thiazolidine-4-carboxylic acid in high chemical yields. Microwave irradiation reduced the reaction time.

    9. Natural Products

      Diversity-Oriented Synthesis of Calothrixins and Ellipticines (pages 6953–6962)

      Dattatraya H. Dethe and Ganesh M. Murhade

      Article first published online: 19 SEP 2014 | DOI: 10.1002/ejoc.201402837

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      The divergent synthesis of calothrixins and ellipticines has been accomplished by utilising the one-pot formation of o-diacylarenes as a key intermediate through rearrangement of o-hydroxy ketone monoacyl hydrazones by lead tetraacetate mediated oxidation.

    10. Protecting Groups

      Efficient Transfer of Chelating Amides into Different Types of Esters and Lactones (pages 6963–6974)

      Uwe Jakob, Stephan Mundinger and Willi Bannwarth

      Article first published online: 12 SEP 2014 | DOI: 10.1002/ejoc.201402843

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      Due to their high resonance energy, amides are generally very stable towards solvolysis. However, bispicolylamides can be activated for alcoholysis by an unusual metal coordination involving the electron pair of the amide nitrogen. Herein, we widened the scope of the reaction by transforming the amides into a range of esters and lactones.

    11. Total Synthesis

      Synthesis of the Sesquiterpenes Albicanol, Drimanol, and Drimanic Acid, and the Marine Sesquiterpene Hydroquinone Deoxyspongiaquinol (pages 6975–6982)

      Matthias Göhl and Karlheinz Seifert

      Article first published online: 18 SEP 2014 | DOI: 10.1002/ejoc.201402873

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      The valuable building blocks in the synthesis of various meroterpenes (+)-albicanyl acetate, (+)-albicanol, (+)-drimanol, and (+)-drimanic acid were synthesized through a TiIII-mediated radical cyclization cascade starting from all-trans-farnesol. (+)-Drimanic acid was transformed into the marine sesquiterpene hydroquinone deoxyspongiaquinol. Thus, five natural products were synthesized.

    12. Cross-Coupling Reactions

      Suzuki–Miyaura Coupling of Aryl Chlorides with Arylboronic Acids Using the Morpholine–NiCl2 Catalyst System (pages 6983–6991)

      Taichi Abe, Takashi Mino, Kohei Watanabe and Masami Sakamoto

      Article first published online: 16 SEP 2014 | DOI: 10.1002/ejoc.201402881

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      We report morpholine–NiCl2 as a new catalyst system for the Suzuki–Miyaura coupling of aryl chlorides with aryl- or alkenylboronic acids to give biaryl compounds. This catalyst system is easy to apply on a large scale because of its easy preparation and the use of inexpensive reagents, and has broad substrate scope. Analysis of the residual nickel showed only 9.7 ppm remaining after work-up.

    13. Alkaloids

      A Glycal Approach to the Synthesis of Steviamine Analogues (pages 6992–6999)

      Venkatesan Santhanam and Namakkal G. Ramesh

      Article first published online: 24 SEP 2014 | DOI: 10.1002/ejoc.201402943

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      We present the synthesis of two new diastereomers of steviamine, an indolizidine alkaloid isolated from Stevia rebaudiana.

    14. Prins Reactions

      Toward Pyridine–Heterocycle Patterns through Prins and Aza-Prins Cyclisations: Application to a Short Synthesis of (±)-Anabasine (pages 7000–7005)

      Olivier Colin, Christine Greck, Damien Prim and Christine Thomassigny

      Article first published online: 15 SEP 2014 | DOI: 10.1002/ejoc.201402971

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      The (aza)-Prins cyclisation has been applied to several pyridine carbaldehydes, opening the way to an easy access to bisheterocycles. The method was effective for the synthesis of anabasine in two steps.

    15. Heterocyclic Rearrangements

      The Boulton–Katritzky Reaction: A Kinetic Study of the Effect of 5-Nitrogen Substituents on the Rearrangement of Some (Z)-Phenylhydrazones of 3-Benzoyl-1,2,4-oxadiazoles (pages 7006–7014)

      Vincenzo Frenna, Antonio Palumbo Piccionello, Barbara Cosimelli, Franco Ghelfi and Domenico Spinelli

      Article first published online: 24 SEP 2014 | DOI: 10.1002/ejoc.201402569

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      The kinetics of the Buolton–Katritzky reaction of nitrogen-substituted phenylhydrazones of 3-benzoyl-1,2,4-oxadiazole to give the relevant triazoles have been examined in a wide range of pS+. The effect of substituents on three different pathways was elucidated.

    16. Anion Recognition

      Sulfate Encapsulation in Supramolecular Structures from L-Asparagine-Derived 2,5-Diketopiperazine Scaffolds: Anion Binding (pages 7015–7022)

      Santhosh Reddy Naini, Roger A. Lalancette, Olga Gorlova, Kallaganti V. S. Ramakrishna, Jhillu Singh Yadav and Subramania Ranganathan

      Article first published online: 24 SEP 2014 | DOI: 10.1002/ejoc.201402610

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      We report a new sulfate receptor, anchored onto 2,5-diketopiperazine units, which results in the formation of two types of supramolecules; one in which the sulfate ion guest fits snugly into extended cavities and the other in which the guest is sandwiched between layers. In each case, the anion is held by six hydrogen bonds from the host. Job plots and association constants were calculated.

    17. Lewis Acid Promoted Cyclization

      Six-Membered Ring Formation from Lewis Acid Promoted Reactions of 2-Substituted 2-Alkenyl Amides and Esters of Ethenetricarboxylate (pages 7023–7033)

      Shoko Yamazaki, Kohta Ueda, Yugo Fukushima, Akiya Ogawa and Kiyomi Kakiuchi

      Article first published online: 17 SEP 2014 | DOI: 10.1002/ejoc.201402637

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      The Lewis acid promoted reactions of 2-substituted 2-propenyl amides and allenyl esters of ethenetricarboxylate gave six-membered-ring heterocycles as the major products. In the reactions of the 2-substituted 2-propenyl amides, elimination products were obtained selectively instead of the substitution products.

    18. Asymmetric Transfer Hydrogenation

      Microwave-Enhanced Asymmetric Transfer Hydrogenation of N-(tert-Butylsulfinyl)imines (pages 7034–7038)

      Óscar Pablo, David Guijarro and Miguel Yus

      Article first published online: 18 SEP 2014 | DOI: 10.1002/ejoc.201402884

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      Microwave irradiation promotes the asymmetric transfer hydrogenation of N-(tert-butylsulfinyl)imines in 2-propanol catalysed by a ruthenium complex bearing an achiral β-amino alcohol as ligand. After desulfinylation, α-branched primary amines containing aromatic, heteroaromatic and aliphatic substituents are obtained in excellent yields and with enantiomeric excesses of up to 96 %.

    19. Dipyrromethanes

      Reactivity of Dipyrromethanes towards Azoalkenes: Synthesis of Functionalized Dipyrromethanes, Calix[4]pyrroles, and Bilanes (pages 7039–7048)

      Susana M. M. Lopes, Américo Lemos and Teresa M. V. D. Pinho e Melo

      Article first published online: 19 SEP 2014 | DOI: 10.1002/ejoc.201402944

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      The hetero-Diels–Alder reaction of dipyrromethanes and azoalkenes was explored as the key step for the synthesis of new dipyrromethanes, calix[4]pyrroles, and bilanes.

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