Advanced Synthesis & Catalysis

Copyright © 2013 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Cover image for Vol. 354 Issue 16

November 12, 2012

Volume 354, Issue 16

Pages 2889–3126

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Communications
    5. Full Papers
    6. Updates
    1. Cover Picture: (Adv. Synth. Catal. 16/2012) (page 2889)

      Article first published online: 9 NOV 2012 | DOI: 10.1002/adsc.201290031

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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. Communications
    5. Full Papers
    6. Updates
    1. Graphical Abstract: Adv. Synth. Catal. 16/2012 (pages 2891–2897)

      Article first published online: 9 NOV 2012 | DOI: 10.1002/adsc.201290032

  3. Communications

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Communications
    5. Full Papers
    6. Updates
    1. A Cooperative Catalytic System of Platinum/Iridium Alloyed Nanoclusters and a Dimeric Catechol Derivative: An Efficient Synthesis of Quinazolines Through a Sequential Aerobic Oxidative Process (pages 2899–2904)

      Hao Yuan, Woo-Jin Yoo, Hiroyuki Miyamura and Shū Kobayashi

      Article first published online: 30 OCT 2012 | DOI: 10.1002/adsc.201200880

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    2. A Polystyrene-Supported, Highly Recyclable Squaramide Organocatalyst for the Enantioselective Michael Addition of 1,3-Dicarbonyl Compounds to β-Nitrostyrenes (pages 2905–2910)

      Pinar Kasaplar, Paola Riente, Caroline Hartmann and Miquel A. Pericàs

      Article first published online: 5 OCT 2012 | DOI: 10.1002/adsc.201200526

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    3. Solid-Supported Rhodium(0) Nano-/Microparticles: An Efficient Ligand-Free Heterogeneous Catalyst for Microwave-Assisted Suzuki–Miyaura Cross-Coupling Reaction (pages 2911–2915)

      Nitul Ranjan Guha, Chennayala Bal Reddy, Nidhi Aggarwal, Dharminder Sharma, Arun K. Shil, Bandna and Pralay Das

      Article first published online: 4 NOV 2012 | DOI: 10.1002/adsc.201200418

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    4. Rhodium-Catalyzed Oxidative ortho-Acylation of Aryl Ketone O-Methyl Oximes with Aryl and Alkyl Aldehydes (pages 2916–2920)

      Yaxi Yang, Bing Zhou and Yuanchao Li

      Article first published online: 30 OCT 2012 | DOI: 10.1002/adsc.201200401

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    5. Asymmetric Intramolecular C[BOND]H Insertion of α-Diazoacetamides in Water by Dirhodium(II) Catalysts Derived from Natural Amino Acids (pages 2921–2927)

      Nuno R. Candeias, Carolina Carias, Luis F. R. Gomes, Vânia André, M. Teresa Duarte, Pedro M. P. Gois and Carlos A. M. Afonso

      Article first published online: 10 OCT 2012 | DOI: 10.1002/adsc.201200101

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    6. Palladium-Catalyzed C[BOND]N Cross-Coupling of N′-Monosubstituted Sulfondiimines with Aryl Bromides (pages 2928–2932)

      Mathieu Candy, Rebekka Anna Bohmann and Carsten Bolm

      Article first published online: 4 NOV 2012 | DOI: 10.1002/adsc.201200754

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    7. A Novel Rhodium-Catalyzed Cascade Cyclization: Direct Synthesis of 3-Substituted Phthalides from Aldehydes and Aromatic Acids (pages 2933–2938)

      Xianying Shi and Chao-Jun Li

      Article first published online: 30 OCT 2012 | DOI: 10.1002/adsc.201200690

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    8. A Domino Desulfitative Coupling/Acylation/Hydration Process Cocatalyzed by Copper(I) and Palladium(II): Synthesis of Highly Substituted and Functionalized Pyrimidines (pages 2939–2948)

      Zheng-Jun Quan, Wang-Hua Hu, Xiao-Dong Jia, Zhang Zhang, Yu-Xia Da and Xi-Cun Wang

      Article first published online: 4 NOV 2012 | DOI: 10.1002/adsc.201200402

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    9. Iron-Catalyzed Amidation of Aldehydes with N-Chloroamines (pages 2949–2953)

      Andrea Porcheddu and Lidia De Luca

      Article first published online: 30 OCT 2012 | DOI: 10.1002/adsc.201200659

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    10. The First Catalytic, Enantioselective Aza-Henry Reaction of an Unactivated Cyclic Imine (pages 2954–2958)

      Nilupa R. Amarasinghe, Peter Turner and Matthew H. Todd

      Article first published online: 30 OCT 2012 | DOI: 10.1002/adsc.201200558

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    11. Dehydrogenative Silylation of Terminal Alkynes with Hydrosilanes under Zinc–Pyridine Catalysis (pages 2959–2964)

      Teruhisa Tsuchimoto, Masakazu Fujii, Yoshihiko Iketani and Masaru Sekine

      Article first published online: 10 OCT 2012 | DOI: 10.1002/adsc.201200310

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    12. Organocatalytic Asymmetric Vinylogous Michael Addition of Dicyanoolefins to Imine Intermediates Generated in situ from Arenesulfonylalkylindoles (pages 2965–2970)

      Xing-Li Zhu, Wu-Jun He, Liang-Liang Yu, Chang-Wu Cai, Zong-Le Zuo, Da-Bin Qin, Quan-Zhong Liu and Lin-Hai Jing

      Article first published online: 30 OCT 2012 | DOI: 10.1002/adsc.201200286

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    13. Asymmetric α-Amination of Aldehydes Catalyzed by PS-Diphenylprolinol Silyl Ethers: Remediation of Catalyst Deactivation for Continuous Flow Operation (pages 2971–2976)

      Xinyuan Fan, Sonia Sayalero and Miquel A. Pericàs

      Article first published online: 30 OCT 2012 | DOI: 10.1002/adsc.201200887

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    14. Organocatalytic Enantioselective Aza-Michael Addition of Purine Bases to α,β-Unsaturated Ketones (pages 2977–2984)

      Hao Wu, Zhiqing Tian, Lili Zhang, Yaodong Huang and Yongmei Wang

      Article first published online: 4 NOV 2012 | DOI: 10.1002/adsc.201200488

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    15. Transition Metal-Free α-C(sp3)[BOND]H Bond Functionalization of Amines by Oxidative Cross Dehydrogenative Coupling Reaction: Simple and Direct Access to C-4-Alkylated 3,4-Dihydroquinazoline Derivatives (pages 2985–2991)

      R. Arun Kumar, G. Saidulu, K. Rajendra Prasad, G. Sathish Kumar, B. Sridhar and K. Rajender Reddy

      Article first published online: 4 NOV 2012 | DOI: 10.1002/adsc.201200679

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    16. Cyanide as a Powerful Catalyst for Facile Preparation of 2-Substituted Benzoxazoles via Aerobic Oxidation (pages 2992–2996)

      Yeon Ho Cho, Chun-Young Lee, Deok-Chan Ha and Cheol-Hong Cheon

      Article first published online: 30 OCT 2012 | DOI: 10.1002/adsc.201200684

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  4. Full Papers

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Communications
    5. Full Papers
    6. Updates
    1. The Catalytic Potential of Coptis japonica NCS2 Revealed – Development and Utilisation of a Fluorescamine-Based Assay (pages 2997–3008)

      Thomas Pesnot, Markus C. Gershater, John M. Ward and Helen C. Hailes

      Article first published online: 4 NOV 2012 | DOI: 10.1002/adsc.201200641

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    2. An Esterase with Superior Activity and Enantioselectivity towards 1,2-O-Isopropylideneglycerol Esters Obtained by Protein Design (pages 3009–3015)

      Luis F. Godinho, Carlos R. Reis, Ronald van Merkerk, Gerrit J. Poelarends and Wim J. Quax

      Article first published online: 4 NOV 2012 | DOI: 10.1002/adsc.201200211

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    3. Poly(styrene) Resin-Supported Cobalt(III) Salen Cyclic Oligomers as Active Heterogeneous HKR Catalysts (pages 3016–3024)

      Michael G. C. Kahn, Joakim H. Stenlid and Marcus Weck

      Article first published online: 4 NOV 2012 | DOI: 10.1002/adsc.201200528

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    4. Modular P[BOND]OP Ligands in Rhodium-Mediated Asymmetric Hydrogenation: A Comparative Catalysis Study (pages 3025–3035)

      José L. Núñez-Rico, Pablo Etayo, Héctor Fernández-Pérez and Anton Vidal-Ferran

      Article first published online: 4 NOV 2012 | DOI: 10.1002/adsc.201200477

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    5. Ruthenium Phenylindenyl Complex as an Efficient Transfer Hydrogenation Catalyst (pages 3036–3044)

      Simone Manzini, César A. Urbina Blanco and Steven P. Nolan

      Article first published online: 4 NOV 2012 | DOI: 10.1002/adsc.201200411

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    6. Acceptorless and Base-Free Dehydrogenation of Alcohols and Amines using Ruthenium-Hydride Complexes (pages 3045–3053)

      Senthilkumar Muthaiah and Soon Hyeok Hong

      Article first published online: 4 NOV 2012 | DOI: 10.1002/adsc.201200532

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    7. Cesium Carbonate-Promoted Hydroamidation of Alkynes: Enamides, Indoles and the Effect of Iron(III) Chloride (pages 3054–3064)

      María Teresa Herrero, Jokin Díaz de Sarralde, Raul SanMartin, Laura Bravo and Esther Domínguez

      Article first published online: 4 NOV 2012 | DOI: 10.1002/adsc.201200430

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    8. Aminocarbonylation of (Hetero)aryl Bromides with Ammonia and Amines using a Palladium/DalPhos Catalyst System (pages 3065–3070)

      Pamela G. Alsabeh, Mark Stradiotto, Helfried Neumann and Matthias Beller

      Article first published online: 4 NOV 2012 | DOI: 10.1002/adsc.201200580

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    9. A Facile Route to Benzo[a]fluorenes via a Palladium-Catalyzed Reaction of 2-Alkynylbromobenzene with 2-(2-Alkynylphenyl)malonate (pages 3071–3077)

      Yong Luo, Xiaolin Pan and Jie Wu

      Article first published online: 4 NOV 2012 | DOI: 10.1002/adsc.201200606

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    10. Chiral Primary Amine Tagged to Ionic Group as Reusable Organocatalyst for Asymmetric Michael Reactions of C-Nucleophiles with α,β-Unsaturated Ketones (pages 3078–3086)

      Alexander S. Kucherenko, Dmitry E. Siyutkin, Albert G. Nigmatov, Alexander O. Chizhov and Sergei G. Zlotin

      Article first published online: 4 NOV 2012 | DOI: 10.1002/adsc.201200338

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    11. Synthesis of Benzoindolines via a Copper-Catalyzed Reaction of 1-Bromoethynyl-2-(cyclopropylidenemethyl)arenes with N-Allylsulfonamide (pages 3087–3094)

      Shaoyu Li, Zhiming Li and Jie Wu

      Article first published online: 6 NOV 2012 | DOI: 10.1002/adsc.201200374

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    12. Diastereoselective Synthesis of Pyrazolines using a Bifunctional Brønsted Acidic Ionic Liquid under Solvent-Free Conditions (pages 3095–3104)

      Shirin Safaei, Iraj Mohammadpoor-Baltork, Ahmad R. Khosropour, Majid Moghadam, Shahram Tangestaninejad and Valiollah Mirkhani

      Article first published online: 4 NOV 2012 | DOI: 10.1002/adsc.201200191

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  5. Updates

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Communications
    5. Full Papers
    6. Updates
    1. A General and Efficient Method for the Alkoxycarbonylation of α-Chloro Ketones (pages 3105–3114)

      Benoit Wahl, Hélène Bonin, André Mortreux, Steven Giboulot, Frédéric Liron, Giovanni Poli and Mathieu Sauthier

      Article first published online: 10 OCT 2012 | DOI: 10.1002/adsc.201200378

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    2. Combining in situ Generated Chiral Silicon Lewis Acid and Chiral Brønsted Acid Catalysts for [3+2] Cycloadditions: Cooperative Catalysis as a Convenient Enantioselective Route to Pyrazolidines (pages 3115–3121)

      Olga V. Serdyuk, Alexandru Zamfir, Frank Hampel and Svetlana B. Tsogoeva

      Article first published online: 10 OCT 2012 | DOI: 10.1002/adsc.201200293

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    3. Palladium-Catalyzed Asymmetric 1,4-Addition of Diarylphosphines to Nitroalkenes for the Synthesis of Chiral P,N-Compounds (pages 3122–3126)

      Jian-Jun Feng, Miao Huang, Zi-Qi Lin and Wei-Liang Duan

      Article first published online: 4 NOV 2012 | DOI: 10.1002/adsc.201200133

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