Advanced Synthesis & Catalysis

Cover image for Vol. 354 Issue 11‐12

August 13, 2012

Volume 354, Issue 11-12

Pages 2061–2347

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Corrigendum
    5. Communications
    6. Full Papers
    7. Updates
    1. You have free access to this content
      Cover Picture: (Adv. Synth. Catal. 11-12/2012) (page 2061)

      Version of Record online: 10 AUG 2012 | DOI: 10.1002/adsc.201290023

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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. Corrigendum
    5. Communications
    6. Full Papers
    7. Updates
  3. Corrigendum

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Corrigendum
    5. Communications
    6. Full Papers
    7. Updates
    1. You have free access to this content
      Corrigendum: Metal-Free, Radical Addition to Alkenes via Desulfitative Chlorine Atom Transfer (page 2070)

      Lidong Cao, Karin Weidner and Philippe Renaud

      Version of Record online: 10 AUG 2012 | DOI: 10.1002/adsc.201290025

      This article corrects:

      Metal-Free, Radical Addition to Alkenes via Desulfitative Chlorine Atom Transfer

      Vol. 353, Issue 18, 3467–3472, Version of Record online: 13 DEC 2011

  4. Communications

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Corrigendum
    5. Communications
    6. Full Papers
    7. Updates
    1. Cooperative Heterogeneous Organocatalysis and Homogeneous Metal Catalysis for the One-Pot Regioselective Synthesis of 2-Pyridones (pages 2084–2088)

      Christophe Allais, Olivier Baslé, Jean-Marie Grassot, Maxime Fontaine, Stéphane Anguille, Jean Rodriguez and Thierry Constantieux

      Version of Record online: 4 JUL 2012 | DOI: 10.1002/adsc.201200367

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    2. Asymmetric Hydrogenation of N-Arylimines Catalyzed by the Xyl-Skewphos/DPEN-Ruthenium(II) Complex (pages 2089–2095)

      Noriyoshi Arai, Noriyuki Utsumi, Yuki Matsumoto, Kunihiko Murata, Kunihiko Tsutsumi and Takeshi Ohkuma

      Version of Record online: 29 JUL 2012 | DOI: 10.1002/adsc.201200464

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    3. Catalytic Asymmetric Friedel–Crafts Reaction of Activated Phenols and 4-Oxo-4-arylbutenoates (pages 2096–2100)

      Sha Bai, Xiaohua Liu, Zhen Wang, Weidi Cao, Lili Lin and Xiaoming Feng

      Version of Record online: 29 JUL 2012 | DOI: 10.1002/adsc.201200341

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    4. Conformationally Rigid Chiral Pyridine N-Oxides as Organocatalyst: Asymmetric Allylation of Aldehydes (pages 2101–2106)

      Elumalai Gnanamani, Nagamalla Someshwar and Chinnasamy Ramaraj Ramanathan

      Version of Record online: 6 JUL 2012 | DOI: 10.1002/adsc.201200115

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    5. Palladium-Catalyzed Aerobic Oxidative Coupling of Acyl Chlorides with Arylboronic Acids (pages 2117–2122)

      Jiuxi Chen, Yong Peng, Miaochang Liu, Jinchang Ding, Weike Su and Huayue Wu

      Version of Record online: 31 JUL 2012 | DOI: 10.1002/adsc.201100971

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    6. A Metal-Free Sulfenylation and Bromosulfenylation of Indoles: Controllable Synthesis of 3-Arylthioindoles and 2-Bromo-3-arylthioindoles (pages 2123–2128)

      Dayun Huang, Jiuxi Chen, Weixing Dan, Jinchang Ding, Miaochang Liu and Huayue Wu

      Version of Record online: 31 JUL 2012 | DOI: 10.1002/adsc.201200227

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    7. Palladium-Catalyzed 1,4-Addition of Carboxylic Acids to Butadiene Monoxide (pages 2129–2134)

      Akiyuki Hamasaki, Shuhei Maruta, Aki Nakamura and Makoto Tokunaga

      Version of Record online: 31 JUL 2012 | DOI: 10.1002/adsc.201200059

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    8. Palladium-Catalyzed C-2 Selective C[BOND]H Olefination of Pyridines (pages 2135–2140)

      Ping Wen, Yanmei Li, Kang Zhou, Chao Ma, Xiaobo Lan, Chaowei Ma and Guosheng Huang

      Version of Record online: 6 AUG 2012 | DOI: 10.1002/adsc.201200195

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    9. Lewis Acid-Catalyzed Conjugate Addition of sp3 C[BOND]H Bonds to Methylenemalononitriles (pages 2146–2150)

      Bo Qian, Dengjian Shi, Lei Yang and Hanmin Huang

      Version of Record online: 31 JUL 2012 | DOI: 10.1002/adsc.201200285

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    10. Highly Enantioselective Michael Addition of 2-Oxindole- 3-carboxylate Esters to Nitroolefins Promoted by Cinchona Alkaloid-Thiourea-Brønsted Acid Cocatalysts (pages 2151–2156)

      Xianjie Chen, Wei Zhu, Wangke Qian, Enguang Feng, Yu Zhou, Jinfang Wang, Hualiang Jiang, Zhu-Jun Yao and Hong Liu

      Version of Record online: 31 JUL 2012 | DOI: 10.1002/adsc.201200206

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    11. Photochemically Induced Silylacylations of Alkynes with Acylsilanes (pages 2157–2161)

      Hui-Jun Zhang, Peter Becker, He Huang, Ramona Pirwerdjan, Fang-Fang Pan and Carsten Bolm

      Version of Record online: 2 JUL 2012 | DOI: 10.1002/adsc.201200510

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  5. Full Papers

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Corrigendum
    5. Communications
    6. Full Papers
    7. Updates
    1. Tetraflic Acid (1,1,2,2-Tetrafluoroethanesulfonic Acid, HC2F4SO3H) and Gallium Tetraflate as Effective Catalysts in Organic Synthesis (pages 2163–2171)

      G. K. Surya Prakash, Thomas Mathew, Chiradeep Panja, Aditya Kulkarni, George A. Olah and Mark A. Harmer

      Version of Record online: 29 JUL 2012 | DOI: 10.1002/adsc.201200111

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    2. Regio- and Stereoselective Hydroxylation of Optically Active α-Ionone Enantiomers by Engineered Cytochrome P450 BM3 Mutants (pages 2172–2184)

      Harini Venkataraman, Stephanie B. A. de Beer, Daan P. Geerke, Nico P. E. Vermeulen and Jan N. M. Commandeur

      Version of Record online: 29 JUL 2012 | DOI: 10.1002/adsc.201200067

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    3. Nitrile Reductase from Geobacillus kaustophilus: A Potential Catalyst for a New Nitrile Biotransformation Reaction (pages 2191–2198)

      Birgit Wilding, Margit Winkler, Barbara Petschacher, Regina Kratzer, Anton Glieder and Norbert Klempier

      Version of Record online: 29 JUL 2012 | DOI: 10.1002/adsc.201200109

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    4. Organocatalytic Asymmetric Synthesis of β-Aryl-β-isocyano Esters (pages 2199–2210)

      Fabio Morana, Andrea Basso, Marco Bella, Renata Riva and Luca Banfi

      Version of Record online: 6 JUL 2012 | DOI: 10.1002/adsc.201200140

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    5. Iodine-Catalyzed, Stereo- and Regioselective Synthesis of 4-Arylidine-4H-benzo[d][1,3]oxazines and their Applications for the Synthesis of Quinazoline 3-Oxides (pages 2218–2228)

      Wen-Chun Lee, Ho-Chuan Shen, Wan-Ping Hu, Wei-Sheng Lo, Chebrolu Murali, Jaya Kishore Vandavasi and Jeh-Jeng Wang

      Version of Record online: 6 JUL 2012 | DOI: 10.1002/adsc.201200018

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    6. One-Pot Tandem Synthesis of 2-Arylbenzoxazole Derivatives via Copper-Catalyzed C[BOND]N and C[BOND]O Bond Formation (pages 2229–2240)

      Veerababurao Kavala, Donala Janreddy, Mustafa J. Raihan, Chun-Wei Kuo, Chintakunta Ramesh and Ching-Fa Yao

      Version of Record online: 6 JUL 2012 | DOI: 10.1002/adsc.201200164

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    7. Oxy Effects on the Platinum-Catalyzed Carbo- and Oxacyclizations of 2-Oxiranyl-1-(1-oxyalk-2-ynyl)benzenes (pages 2241–2250)

      Rupsha Chaudhuri, Samir Kundlik Pawar, Kamalkishore Pati and Rai-Shung Liu

      Version of Record online: 29 JUL 2012 | DOI: 10.1002/adsc.201200187

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    8. The Halonium Ion-Mediated C[BOND]C Bond Cleavage of Cyclohexene-Fused Isoxazoline N-Oxides (pages 2251–2263)

      Mustafa J. Raihan, Veerababurao Kavala, Qiao-Zhi Guan, Chun-Wei Kuo, Sunil Kataria, Shifali Shishodia, Donala Janreddy, Pateliya Mujjamil Habib and Ching-Fa Yao

      Version of Record online: 6 JUL 2012 | DOI: 10.1002/adsc.201200217

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    9. 1,10-Phenanthroline-Catalyzed Tandem Reaction of 2-Iodoanilines with Isothiocyanates in Water (pages 2283–2287)

      Wu Zhang, Yun Yue, Dan Yu, Lei Song, Yang-Yang Xu, Yu-Jie Tian and Yu-Jun Guo

      Version of Record online: 6 AUG 2012 | DOI: 10.1002/adsc.201200175

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    10. Selective para-Cyanation of Alkoxy- and Benzyloxy-Substituted Benzenes with Potassium Ferricyanide Promoted by Copper(II) Nitrate and Iodine (pages 2301–2308)

      Yunlai Ren, Mengjie Yan, Shuang Zhao, Jianji Wang, Junying Ma, Xinzhe Tian and Weiping Yin

      Version of Record online: 31 JUL 2012 | DOI: 10.1002/adsc.201200235

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  6. Updates

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Corrigendum
    5. Communications
    6. Full Papers
    7. Updates
    1. A Polymer-Supported Chiral Fluorinated Dirhodium(II) Complex for Asymmetric Amination of Silyl Enol Ethers (pages 2331–2338)

      Tadashi Oohara, Hisanori Nambu, Masahiro Anada, Koji Takeda and Shunichi Hashimoto

      Version of Record online: 6 AUG 2012 | DOI: 10.1002/adsc.201200219

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    2. Exclusive 1,2-Aryl Shift in Platinum(II) Chloride-Catalyzed Cyclization of 1-(Indol-2-yl)-2,3-allenols (pages 2339–2347)

      Wangqing Kong, Youai Qiu, Xue Zhang, Chunling Fu and Shengming Ma

      Version of Record online: 29 JUL 2012 | DOI: 10.1002/adsc.201100935

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