Advanced Synthesis & Catalysis

Cover image for Vol. 354 Issue 14‐15

October 8, 2012

Volume 354, Issue 14-15

Pages 2573–2885

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Review
    5. Communications
    6. Full Papers
    7. Updates
    1. You have free access to this content
      Cover Picture: (Adv. Synth. Catal. 14-15/2012) (page 2573)

      Version of Record online: 12 OCT 2012 | DOI: 10.1002/adsc.201290029

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      The cover picture, provided by Qi-Lin Zhou, shows the example of an exceptionally highly efficient chiral catalyst. The catalyst is a very stable dihydride iridium complex of a tridentate chiral spiro P-N-N ligand based on the 1,1′-spirobiindane skeleton, which exhibits excellent enantioselectivity and extremely high turnover number (in excess of one million) for the hydrogenation of both aryl ketones and β-aryl-β-keto esters. Although little is known about the mechanism of this iridiumcatalyzed carbonyl group hydrogenation reaction, a non-classical metal[BOND]ligand bifunctional mechanism deserves to be recommended to interpret the high efficiency of this catalyst. With the help of KO-t-Bu and under an H2 atmosphere, the dihydride iridium complex is converted to a trihydride iridium complex. After combination of the substrate with the trihydride iridium complex, a cyclic six-membered transition state is formed. The hydridic Ir[BOND]H and protic N[BOND]H of the catalyst are simultaneously transferred to the carbonyl[BOND]oxygen double bond of the substrate, resulting in a chiral alcohol and a hydrido amido iridium complex. Finally, the hydrido amido iridium complex is hydrogenated with H2 to regenerate the trihydride iridium complex.

  2. Contents

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Review
    5. Communications
    6. Full Papers
    7. Updates
  3. Review

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Review
    5. Communications
    6. Full Papers
    7. Updates
  4. Communications

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Review
    5. Communications
    6. Full Papers
    7. Updates
    1. Hydrosilylation of Aldehydes and Ketones Catalyzed by an N-Heterocyclic Carbene-Nickel Hydride Complex under Mild Conditions (pages 2619–2624)

      Linus P. Bheeter, Mickaël Henrion, Lydia Brelot, Christophe Darcel, Michael J. Chetcuti, Jean-Baptiste Sortais and Vincent Ritleng

      Version of Record online: 5 OCT 2012 | DOI: 10.1002/adsc.201200460

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    2. Retropinacol/Cross-Pinacol Coupling Reactions – A Catalytic Access to 1,2-Unsymmetrical Diols (pages 2648–2652)

      Ulf Scheffler, Reinhard Stößer and Rainer Mahrwald

      Version of Record online: 28 SEP 2012 | DOI: 10.1002/adsc.201200358

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    3. Catalytic C[BOND]Se Bond Formation under Very Mild Conditions for the Two-Step, One-Pot Synthesis of Aryl Selenoacetates (pages 2653–2658)

      Konstantin Grenader, Björn Schüpbach, Annabell Peters, Oliver Kümmel, Oliver Halter and Andreas Terfort

      Version of Record online: 5 OCT 2012 | DOI: 10.1002/adsc.201200486

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    4. Copper-Catalyzed Synthesis of Alkylphosphonates from H-Phosphonates and N-Tosylhydrazones (pages 2659–2664)

      Wenjun Miao, Yuzhen Gao, Xueqin Li, Yuxing Gao, Guo Tang and Yufen Zhao

      Version of Record online: 4 OCT 2012 | DOI: 10.1002/adsc.201200295

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    5. Selective Hydrogenation of Nitroarenes and Olefins over Rhodium Nanoparticles on Hydroxyapatite (pages 2689–2694)

      Lei Huang, Pingfei Luo, Weige Pei, Xiaoyun Liu, Yong Wang, Jun Wang, Weihong Xing and Jun Huang

      Version of Record online: 28 SEP 2012 | DOI: 10.1002/adsc.201200330

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    6. Unexpected N-Demethylation of Oxymorphone and Oxycodone N-Oxides Mediated by the Burgess Reagent: Direct Synthesis of Naltrexone, Naloxone, and Other Antagonists from Oxymorphone (pages 2706–2712)

      Lukas Werner, Martina Wernerova, Ales Machara, Mary Ann Endoma-Arias, Jan Duchek, David R. Adams , D. Phillip Cox and Tomas Hudlicky

      Version of Record online: 4 OCT 2012 | DOI: 10.1002/adsc.201200676

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  5. Full Papers

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Review
    5. Communications
    6. Full Papers
    7. Updates
    1. Palladium-Catalyzed Asymmetric Hydrogenation of N-Hydroxy-α-imino Phosphonates Using Brønsted Acid as Activator: The First Catalytic Enantioselective Approach to Chiral N-Hydroxy-α-amino Phosphonates (pages 2727–2733)

      Nataliya S. Goulioukina, Ilya A. Shergold, Grigorii N. Bondarenko, Mikhail M. Ilyin, Vadim A. Davankov and Irina P. Beletskaya

      Version of Record online: 5 OCT 2012 | DOI: 10.1002/adsc.201200170

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    2. Catalytic and Structural Studies of Hoveyda–Grubbs Type Pre-Catalysts Bearing Modified Ether Ligands (pages 2734–2742)

      Stefano Guidone, Enguerrand Blondiaux, Cezary Samojłowicz, Łukasz Gułajski, Mariusz Kędziorek, Maura Malińska, Aleksandra Pazio, Krzysztof Woźniak, Karol Grela, Angelino Doppiu and Catherine S. J. Cazin

      Version of Record online: 4 OCT 2012 | DOI: 10.1002/adsc.201200385

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    3. A Unique Ruthenium Carbyne Complex: A Highly Thermo-endurable Catalyst for Olefin Metathesis (pages 2743–2750)

      Mingbo Shao, Lu Zheng, Weixia Qiao, Jingjing Wang and Jianhui Wang

      Version of Record online: 28 SEP 2012 | DOI: 10.1002/adsc.201200119

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    4. Selective Palladium-Catalyzed Direct Arylation of Furo[3,2-b]pyridines (pages 2751–2756)

      Amandine Carrër, Patricia Rousselle, Jean-Claude Florent and Emmanuel Bertounesque

      Version of Record online: 5 OCT 2012 | DOI: 10.1002/adsc.201200543

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    5. Desulfurization Strategy in the Construction of Azoles Possessing Additional Nitrogen, Oxygen or Sulfur using a Copper(I) Catalyst (pages 2757–2770)

      Srimanta Guin, Saroj Kumar Rout, Anupal Gogoi, Shyamapada Nandi, Krishna Kanta Ghara and Bhisma K. Patel

      Version of Record online: 28 SEP 2012 | DOI: 10.1002/adsc.201200408

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    6. Microwave-Promoted Suzuki–Miyaura Cross-Coupling of Aryl Imidazolylsulfonates in Water (pages 2771–2776)

      José F. Cívicos, Diego A. Alonso and Carmen Nájera

      Version of Record online: 28 SEP 2012 | DOI: 10.1002/adsc.201200364

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    7. Ullmann Homocoupling Catalysed by Gold Nanoparticles in Water and Ionic Liquid (pages 2777–2788)

      Antonio Monopoli, Pietro Cotugno, Gerardo Palazzo, Nicoletta Ditaranto, Bruno Mariano, Nicola Cioffi, Francesco Ciminale and Angelo Nacci

      Version of Record online: 5 OCT 2012 | DOI: 10.1002/adsc.201200422

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    8. On the Mechanism of Asymmetric Epoxidation of Enones Catalyzed by α,α-L-Diarylprolinols: A Theoretical Insight (pages 2789–2796)

      Amedeo Capobianco, Alessio Russo, Alessandra Lattanzi and Andrea Peluso

      Version of Record online: 5 OCT 2012 | DOI: 10.1002/adsc.201200415

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    9. You have full text access to this OnlineOpen article
      Influence of Organic Solvents on Enzymatic Asymmetric Carboligations (pages 2805–2820)

      Tina Gerhards, Ursula Mackfeld, Marco Bocola, Eric von Lieres, Wolfgang Wiechert, Martina Pohl and Dörte Rother

      Version of Record online: 4 OCT 2012 | DOI: 10.1002/adsc.201200284

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    10. Exploitation of a Laccase/Meldola’s Blue System for NAD+ Regeneration in Preparative Scale Hydroxysteroid Dehydrogenase-Catalyzed Oxidations (pages 2821–2828)

      Erica Elisa Ferrandi, Daniela Monti, Ilabahen Patel, Roman Kittl, Dietmar Haltrich, Sergio Riva and Roland Ludwig

      Version of Record online: 5 OCT 2012 | DOI: 10.1002/adsc.201200429

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    11. Palladium-Catalyzed Cross-Coupling of 1-Aminoazoles with Aryl Chlorides: Application to the Synthesis of Unsymmetrical N,N′-Diaryl-1-aminoindoles (pages 2829–2839)

      Etienne Brachet, Samir Messaoudi, Jean-François Peyrat, Jean-Daniel Brion and Mouad Alami

      Version of Record online: 28 SEP 2012 | DOI: 10.1002/adsc.201200440

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  6. Updates

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Review
    5. Communications
    6. Full Papers
    7. Updates
    1. Synthesis of Azocino[5,4-b]indoles via Gold-Catalyzed Intramolecular Alkyne Hydroarylation (pages 2841–2848)

      Vsevolod A. Peshkov, Olga P. Pereshivko and Erik V. Van der Eycken

      Version of Record online: 28 SEP 2012 | DOI: 10.1002/adsc.201200305

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