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Catalysis with gold complexes immobilised on carbon nanotubes by π-π Stacking interactions: Heterogeneous catalysis versus the boomerang effect

Bibliographic reference Vriamont, Charles ; Devillers, Michel ; Riant, Olivier ; Hermans, Sophie. Catalysis with gold complexes immobilised on carbon nanotubes by π-π Stacking interactions: Heterogeneous catalysis versus the boomerang effect. In: Chemistry - A European Journal, Vol. 19, no.36, p. 12009-12017 (2013)
Permanent URL http://hdl.handle.net/2078.1/134624
  1. De Vos Dirk E., Dams Mieke, Sels Bert F., Jacobs Pierre A., Ordered Mesoporous and Microporous Molecular Sieves Functionalized with Transition Metal Complexes as Catalysts for Selective Organic Transformations, 10.1021/cr010368u
  2. Song Choong Eui, Lee Sang-gi, Supported Chiral Catalysts on Inorganic Materials, 10.1021/cr0103625
  3. Leadbeater Nicholas E., Marco Maria, Preparation of Polymer-Supported Ligands and Metal Complexes for Use in Catalysis, 10.1021/cr010361c
  4. Corma Avelino, Garcia Hermenegildo, Crossing the Borders Between Homogeneous and Heterogeneous Catalysis: Developing Recoverable and Reusable Catalytic Systems, 10.1007/s11244-008-9056-5
  5. Choplin Agnès, Quignard Françoise, From supported homogeneous catalysts to heterogeneous molecular catalysts, 10.1016/s0010-8545(98)00062-9
  6. Valkenberg Michael H., Hölderich Wolfgang F., Preparation and use of hybrid organic–inorganic catalysts, 10.1081/cr-120003497
  7. Schaetz Alexander, Zeltner Martin, Stark Wendelin J., Carbon Modifications and Surfaces for Catalytic Organic Transformations, 10.1021/cs300014k
  8. Hirsch Andreas, Funktionalisierung von einwandigen Kohlenstoffnanoröhren, 10.1002/1521-3757(20020603)114:11<1933::aid-ange1933>3.0.co;2-r
  9. Hirsch Andreas, Functionalization of Single-Walled Carbon Nanotubes, 10.1002/1521-3773(20020603)41:11<1853::aid-anie1853>3.0.co;2-n
  10. Singh Prabhpreet, Campidelli Stéphane, Giordani Silvia, Bonifazi Davide, Bianco Alberto, Prato Maurizio, Organic functionalisation and characterisation of single-walled carbon nanotubes, 10.1039/b518111a
  11. Tasis Dimitrios, Tagmatarchis Nikos, Bianco Alberto, Prato Maurizio, Chemistry of Carbon Nanotubes, 10.1021/cr050569o
  12. Balasubramanian Kannan, Burghard Marko, Chemically Functionalized Carbon Nanotubes, 10.1002/smll.200400118
  13. Zhao Yan-Li, Stoddart J. Fraser, Noncovalent Functionalization of Single-Walled Carbon Nanotubes, 10.1021/ar900056z
  14. Huang H., Yuan Q., Shah J.S., Misra R.D.K., A new family of folate-decorated and carbon nanotube-mediated drug delivery system: Synthesis and drug delivery response, 10.1016/j.addr.2011.04.001
  15. Schulz-Drost Christian, Sgobba Vito, Gerhards Christina, Leubner Susanne, Krick Calderon Rafael M., Ruland Andrés, Guldi Dirk M., Innovative anorganisch-organische Nanohybridmaterialien: Ankopplung von Quantenpunkten an Kohlenstoffnanoröhren, 10.1002/ange.200906891
  16. Schulz-Drost Christian, Sgobba Vito, Gerhards Christina, Leubner Susanne, Krick Calderon Rafael M., Ruland Andrés, Guldi Dirk M., Innovative Inorganic-Organic Nanohybrid Materials: Coupling Quantum Dots to Carbon Nanotubes, 10.1002/anie.200906891
  17. Vijayakumar Chakkooth, Balan Bijitha, Kim Mi-Jeong, Takeuchi Masayuki, Noncovalent Functionalization of SWNTs with Azobenzene-Containing Polymers: Solubility, Stability, and Enhancement of Photoresponsive Properties, 10.1021/jp111248r
  18. Janiak Christoph, A critical account on π–π stacking in metal complexes with aromatic nitrogen-containing ligands †, 10.1039/b003010o
  19. Britz David A., Khlobystov Andrei N., Noncovalent interactions of molecules with single walled carbon nanotubes, 10.1039/b507451g
  20. Ito Yoshihiko., Sawamura Masaya., Hayashi Tamio., Catalytic asymmetric aldol reaction: reaction of aldehydes with isocyanoacetate catalyzed by a chiral ferrocenylphosphine-gold(I) complex, 10.1021/ja00280a056
  21. Ito Yoshihiko, Sawamura Masaya, Hayashi Tamio, Asymmetric synthesis of threo- and erythro-sphingosines by asymmetric aldol reaction of α-isocyanoacetate catalyzed by a chiral ferrocenylphosphine-gold(I) complex, 10.1016/s0040-4039(00)80064-7
  22. Pastor Stephen D., Togni Antonio, Asymmetric synthesis with chiral ferrocenylamine ligands: the importance of central chirality, 10.1021/ja00188a075
  23. Togni Antonio, Pastor Stephen D., Chiral cooperativity: the nature of the diastereoselective and enantioselective step in the gold(I)-catalyzed aldol reaction utilizing chiral ferrocenylamine ligands, 10.1021/jo00292a046
  24. Hashmi A. Stephen K., Schwarz Lothar, Choi Ji-Hyun, Frost Tanja M., Eine neue Gold-katalysierte C-C-Bindungsknüpfung, 10.1002/1521-3757(20000703)112:13<2382::aid-ange2382>3.0.co;2-r
  25. Hashmi A. Stephen K., Schwarz Lothar, Choi Ji-Hyun, Frost Tanja M., A New Gold-Catalyzed C−C Bond Formation, 10.1002/1521-3773(20000703)39:13<2285::aid-anie2285>3.0.co;2-f
  26. Hashmi A. Stephen K., Frost Tanja M., Bats J. W., Highly Selective Gold-Catalyzed Arene Synthesis, 10.1021/ja005570d
  27. Hashmi A. Stephen K., Gold-Catalyzed Organic Reactions, 10.1021/cr000436x
  28. Li Zigang, Brouwer Chad, He Chuan, Gold-Catalyzed Organic Transformations, 10.1021/cr068434l
  29. Krause Norbert, Winter Christian, Gold-Catalyzed Nucleophilic Cyclization of Functionalized Allenes: A Powerful Access to Carbo- and Heterocycles, 10.1021/cr1004088
  30. Corma A., Leyva-Pérez A., Sabater Maria J., Gold-Catalyzed Carbon−Heteroatom Bond-Forming Reactions, 10.1021/cr100414u
  31. Jiménez-Núñez Eloísa, Echavarren Antonio M., Gold-Catalyzed Cycloisomerizations of Enynes: A Mechanistic Perspective, 10.1021/cr0684319
  32. Arcadi Antonio, Alternative Synthetic Methods through New Developments in Catalysis by Gold, 10.1021/cr068435d
  33. Aubert Corinne, Fensterbank Louis, Garcia Pierre, Malacria Max, Simonneau Antoine, Transition Metal Catalyzed Cycloisomerizations of 1,n-Allenynes and -Allenenes, 10.1021/cr100376w
  34. Leseurre Lucie, Chao Chung-Meng, Seki Tomohiro, Genin Emilie, Toullec Patrick Y., Genêt Jean-Pierre, Michelet Véronique, Synthesis of functionalized carbo- and heterocycles via gold-catalyzed cycloisomerization reactions of enynes, 10.1016/j.tet.2008.11.105
  35. Raducan Mihai, Rodríguez-Escrich Carles, Cambeiro Xacobe C., Escudero-Adán Eduardo C., Pericàs Miquel A., Echavarren Antonio M., A multipurpose gold(i) precatalyst, 10.1039/c1cc10293a
  36. Nieto-Oberhuber Cristina, López Salomé, Muñoz M. Paz, Jiménez-Núñez Eloísa, Buñuel Elena, Cárdenas Diego J., Echavarren Antonio M., Gold(I)-Catalyzed Intramolecular Cyclopropanation of Dienynes, 10.1002/chem.200501089
  37. Nieto-Oberhuber Cristina, Muñoz M. Paz, López Salomé, Jiménez-Núñez Eloísa, Nevado Cristina, Herrero-Gómez Elena, Raducan Mihai, Echavarren Antonio M., Gold(I)-Catalyzed Cyclizations of 1,6-Enynes: Alkoxycyclizations andexo/endo Skeletal Rearrangements, 10.1002/chem.200501088
  38. Nieto-Oberhuber Cristina, Muñoz M. Paz, Buñuel Elena, Nevado Cristina, Cárdenas Diego J., Echavarren Antonio M., Cationic Gold(I) Complexes: Highly Alkynophilic Catalysts for theexo- andendo-Cyclization of Enynes, 10.1002/ange.200353207
  39. Nieto-Oberhuber Cristina, Muñoz M. Paz, Buñuel Elena, Nevado Cristina, Cárdenas Diego J., Echavarren Antonio M., Cationic Gold(I) Complexes: Highly Alkynophilic Catalysts for theexo- andendo-Cyclization of Enynes, 10.1002/anie.200353207
  40. Nieto-Oberhuber Cristina, López Salomé, Echavarren Antonio M., Intramolecular [4 + 2] Cycloadditions of 1,3-Enynes or Arylalkynes with Alkenes with Highly Reactive Cationic Phosphine Au(I) Complexes, 10.1021/ja042257t
  41. Mézailles Nicolas, Ricard Louis, Gagosz Fabien, Phosphine Gold(I) Bis-(trifluoromethanesulfonyl)imidate Complexes as New Highly Efficient and Air-Stable Catalysts for the Cycloisomerization of Enynes, 10.1021/ol0515917
  42. Soriano Elena, Marco-Contelles José, Mechanistic Insights on the Cycloisomerization of Polyunsaturated Precursors Catalyzed by Platinum and Gold Complexes, 10.1021/ar800200m
  43. Li Changkun, Zeng Yi, Zhang Hang, Feng Jiajie, Zhang Yan, Wang Jianbo, Gold(I)-Catalyzed Cycloisomerization of Enynes Containing Cyclopropenes, 10.1002/ange.201002673
  44. Li Changkun, Zeng Yi, Zhang Hang, Feng Jiajie, Zhang Yan, Wang Jianbo, Gold(I)-Catalyzed Cycloisomerization of Enynes Containing Cyclopropenes, 10.1002/anie.201002673
  45. Hashmi A. Stephen K., Hubbert Christoph, Gold- und Organokatalyse gekoppelt, 10.1002/ange.200906609
  46. Hashmi A. Stephen K., Hubbert Christoph, Gold and Organocatalysis Combined, 10.1002/anie.200906609
  47. López-Carrillo Verónica, Huguet Núria, Mosquera Ángeles, Echavarren Antonio M., Nature of the Intermediates in Gold(I)-Catalyzed Cyclizations of 1,5-Enynes, 10.1002/chem.201101749
  48. Duan Haifeng, Sengupta Sujata, Petersen Jeffrey L., Akhmedov Novruz G., Shi Xiaodong, Triazole−Au(I) Complexes: A New Class of Catalysts with Improved Thermal Stability and Reactivity for Intermolecular Alkyne Hydroamination, 10.1021/ja9041093
  49. Leseurre Lucie, Toullec Patrick Yves, Genêt Jean-Pierre, Michelet Véronique, Gold-Catalyzed Hydroamination/Cycloisomerization Reaction of 1,6-Enynes, 10.1021/ol7017483
  50. Nishina Naoko, Yamamoto Yoshinori, Gold-catalyzed intermolecular hydroalkoxylation of allenes; difference in mechanism between hydroalkoxylation and hydroamination, 10.1016/j.tetlet.2008.05.152
  51. Leyva Antonio, Corma Avelino, Isolable Gold(I) Complexes Having One Low-Coordinating Ligand as Catalysts for the Selective Hydration of Substituted Alkynes at Room Temperature without Acidic Promoters, 10.1021/jo802558e
  52. Hashmi A. Stephen K., Yang Weibo, Rominger Frank, Gold(I)-Catalyzed Formation of Benzo[b]furans from 3-Silyloxy-1,5-enynes, 10.1002/anie.201100989
  53. Hashmi A. Stephen K., Yang Weibo, Rominger Frank, Gold(I)-katalysierte Synthese von Benzo[b]furanen aus 3-Silyloxy-1,5-eninen, 10.1002/ange.201100989
  54. Hashmi A. Stephen K., Yang Weibo, Rominger Frank, Gold(I)-Catalyzed Rearrangement of 3-Silyloxy-1,5-enynes: An Efficient Synthesis of Benzo[b]thiophenes, Dibenzothiophenes, Dibenzofurans, and Indole Derivatives, 10.1002/chem.201200314
  55. Hashmi A. Stephen K., New pathways in the gold-catalyzed cycloisomerization of furanynes, 10.1351/pac-con-09-10-34
  56. Nun Pierrick, Egbert Jonathan D., Oliva-Madrid María-José, Nolan Steven P., Gold(I)-Catalyzed Stereoselective Synthesis of Alkenyl Phosphates by Hydrophosphoryloxylation, 10.1002/chem.201103304
  57. Giordano Roberto, Serp Philippe, Kalck Philippe, Kihn Yolande, Schreiber Joachim, Marhic Christiane, Duvail Jean-Luc, Preparation of Rhodium Catalysts Supported on Carbon Nanotubes by a Surface Mediated Organometallic Reaction, 10.1002/ejic.200390083
  58. Banerjee Sarbajit, Wong Stanislaus S., Structural Characterization, Optical Properties, and Improved Solubility of Carbon Nanotubes Functionalized with Wilkinson's Catalyst, 10.1021/ja026487o
  59. Zhang Yu, Zhang Hong-Bin, Lin Guo-Dong, Chen Ping, Yuan You-Zhu, Tsai K.R., Preparation, characterization and catalytic hydroformylation properties of carbon nanotubes-supported Rh–phosphine catalyst, 10.1016/s0926-860x(99)00229-x
  60. Baleizão C, Vanadyl salen complexes covalently anchored to single-wall carbon nanotubes as heterogeneous catalysts for the cyanosilylation of aldehydes, 10.1016/j.jcat.2003.08.016
  61. Baleizão Carlos, Gigante Bárbara, García Hermenegildo, Corma Avelino, Chiral vanadyl salen complex anchored on supports as recoverable catalysts for the enantioselective cyanosilylation of aldehydes. Comparison among silica, single wall carbon nanotube, activated carbon and imidazolium ion as support, 10.1016/j.tet.2004.08.077
  62. Moghadam Majid, Tangestaninejad Shahram, Mirkhani Valiollah, Mohammadpoor-Baltork Iraj, Mirbagheri Naghmeh Sadat, Molybdenum hexacarbonyl supported on functionalized multi-wall carbon nanotubes: Efficient and highly reusable catalysts for epoxidation of alkenes with tert-butyl hydroperoxide, 10.1016/j.jorganchem.2010.05.008
  63. Moghadam Majid, Tangestaninejad Shahram, Mirkhani Valiollah, Mohammadpoor-Baltork Iraj, Mirjafari Arsalan, Mirbagheri Naghmeh Sadat, Multi-wall carbon nanotubes supported molybdenum hexacarbonyl: An efficient and highly reusable catalyst for epoxidation of alkenes with tert-butyl hydroperoxide, 10.1016/j.molcata.2010.06.016
  64. Nooraeipour Mehdi, Moghadam Majid, Tangestaninejad Shahram, Mirkhani Valiollah, Mohammadpoor-Baltork Iraj, Iravani Nasir, Multi-wall carbon nanotube supported tungsten hexacarbonyl: an efficient and reusable catalyst for epoxidation of alkenes with hydrogen peroxide, 10.1080/00958972.2011.643788
  65. Zakeri Maryam, Moghadam Majid, Mohammadpoor-Baltork Iraj, Tangestaninejad Shahram, Mirkhani Valiollah, Khosropour Ahmad Reza, Multi-wall carbon nanotube supported manganese(III)tetraphenylporphyrin: efficient catalysts for epoxidation of alkenes with NaIO4under various reaction conditions, 10.1080/00958972.2012.666349
  66. Moghadam Majid, Mohammadpoor-Baltork Iraj, Tangestaninejad Shahram, Mirkhani Valiollah, Kargar Hadi, Zeini-Isfahani Nafiseh, Manganese(III) porphyrin supported on multi-wall carbon nanotubes: A highly efficient and reusable biomimetic catalyst for epoxidation of alkenes with sodium periodate, 10.1016/j.poly.2009.08.016
  67. Liu Guiyan, Wu Bin, Zhang Jianzheng, Wang Xiaoli, Shao Mingbo, Wang Jianhui, Controlled Reversible Immobilization of Ru Carbene on Single-Walled Carbon Nanotubes: A New Strategy for Green Catalytic Systems Based on a Solvent Effect on π−π Interaction, 10.1021/ic801111h
  68. Li Fei, Zhang Biaobiao, Li Xiaona, Jiang Yi, Chen Lin, Li Yanqing, Sun Licheng, Highly Efficient Oxidation of Water by a Molecular Catalyst Immobilized on Carbon Nanotubes, 10.1002/ange.201105044
  69. Li Fei, Zhang Biaobiao, Li Xiaona, Jiang Yi, Chen Lin, Li Yanqing, Sun Licheng, Highly Efficient Oxidation of Water by a Molecular Catalyst Immobilized on Carbon Nanotubes, 10.1002/anie.201105044
  70. Xing Liang, Xie Jian-Hua, Chen Yong-Sheng, Wang Li-Xin, Zhou Qi-Lin, Simply Modified Chiral Diphosphine: Catalyst Recyclingvia Non-covalent Absorption on Carbon Nanotubes, 10.1002/adsc.200700617
  71. Tran Phong D., Le Goff Alan, Heidkamp Jonathan, Jousselme Bruno, Guillet Nicolas, Palacin Serge, Dau Holger, Fontecave Marc, Artero Vincent, Noncovalent Modification of Carbon Nanotubes with Pyrene-Functionalized Nickel Complexes: Carbon Monoxide Tolerant Catalysts for Hydrogen Evolution and Uptake, 10.1002/ange.201005427
  72. Tran Phong D., Le Goff Alan, Heidkamp Jonathan, Jousselme Bruno, Guillet Nicolas, Palacin Serge, Dau Holger, Fontecave Marc, Artero Vincent, Noncovalent Modification of Carbon Nanotubes with Pyrene-Functionalized Nickel Complexes: Carbon Monoxide Tolerant Catalysts for Hydrogen Evolution and Uptake, 10.1002/anie.201005427
  73. Schätz Alexander, Reiser Oliver, Stark Wendelin J., Nanoparticles as Semi-Heterogeneous Catalyst Supports, 10.1002/chem.200903462
  74. Nishimura Masato, Ueda Masato, Miyaura Norio, Palladium-catalyzed biaryl-coupling reaction of arylboronic acids in water using hydrophilic phosphine ligands, 10.1016/s0040-4020(02)00576-8
  75. Kyatskaya Svetlana, Galán Mascarós José Ramón, Bogani Lapo, Hennrich Frank, Kappes Manfred, Wernsdorfer Wolfgang, Ruben Mario, Anchoring of Rare-Earth-Based Single-Molecule Magnets on Single-Walled Carbon Nanotubes, 10.1021/ja906165e
  76. Faller J.W., Fontaine Philip P., Ruthenium catalyzed enyne cycloisomerizations and hydroxycyclizations with skeletal rearrangement, 10.1016/j.jorganchem.2006.01.009
  77. Monnier Florian, Vovard-Le Bray Chloé, Castillo Dante, Aubert Vincent, Dérien Sylvie, Dixneuf Pierre H., Toupet Loic, Ienco Andrea, Mealli Carlo, Selective Ruthenium-Catalyzed Transformations of Enynes with Diazoalkanes into Alkenylbicyclo[3.1.0]hexanes, 10.1021/ja0700146
  78. Yamamoto Hirofumi, Nishiyama Mami, Imagawa Hiroshi, Nishizawa Mugio, Hg(OTf)2-Catalyzed cyclization of alkynyl tert-butylcarbonate leading to cyclic enol carbonate, 10.1016/j.tetlet.2006.09.067
  79. Gaillard Sylvain, Bosson Johann, Ramón Rubén S., Nun Pierrick, Slawin Alexandra M. Z., Nolan Steven P., Development of Versatile and Silver-Free Protocols for Gold(I) Catalysis, 10.1002/chem.201001688
  80. Nishizawa Mugio, Yadav Veejendra K., Skwarczynski Mariusz, Takao Hiroko, Imagawa Hiroshi, Sugihara Takumichi, Mercuric Triflate Catalyzed Hydroxylative Carbocyclization of 1,6-Enynes, 10.1021/ol034201u
  81. Buzas Andrea K., Istrate Florin M., Gagosz Fabien, Gold-catalyzed rearrangement of propargylic tert-butyl carbonates, 10.1016/j.tet.2008.11.108