Access the full text.
Sign up today, get DeepDyve free for 14 days.
Loading next page...
/lp/rsc/a-superhydrophobic-mesostructured-silica-as-a-chiral-organometallic-oYJI3dJ9BS
References (62)
-
T. Ohkuma, K. Tsutsumi, Noriyuki Utsumi, N. Arai, R. Noyori, K. Murata (2007)
Asymmetric Hydrogenation of α-Chloro Aromatic Ketones Catalyzed by η6-Arene/TsDPEN−Ruthenium(II) ComplexesOrganic Letters, 9
-
Juan Peng, Yi Yao, Xiaoming Zhang, Can Li, Qihua Yang (2014)
Superhydrophobic mesoporous silica nanospheres achieved via a high level of organo-functionalization.Chemical communications, 50 74
-
O. Kröcher, R. Köppel, M. Fröba, A. Baiker (1998)
Silica Hybrid Gel Catalysts Containing Group(VIII) Transition Metal Complexes: Preparation, Structural, and Catalytic Properties in the Synthesis ofN,N-Dimethylformamide and Methyl Formate from Supercritical Carbon DioxideJournal of Catalysis, 178
-
J. Martins, G. Clarkson, M. Wills (2009)
Ru(II) complexes of N-alkylated TsDPEN ligands in asymmetric transfer hydrogenation of ketones and imines.Organic letters, 11 4
-
B. Seashore-Ludlow, François Saint-Dizier, P. Somfai (2012)
Asymmetric transfer hydrogenation coupled with dynamic kinetic resolution in water: synthesis of anti-β-hydroxy-α-amino acid derivatives.Organic letters, 14 24
-
Doo-Sik Moon, Jin-Kyu Lee (2012)
Tunable synthesis of hierarchical mesoporous silica nanoparticles with radial wrinkle structure.Langmuir : the ACS journal of surfaces and colloids, 28 33
-
Kesong Liu, Xi Yao, Lei Jiang (2010)
Recent developments in bio-inspired special wettability.Chemical Society reviews, 39 8
-
Zhen‐An Qiao, Ling Zhang, Mingyi Guo, Yunlin Liu, Q. Huo (2009)
Synthesis of Mesoporous Silica Nanoparticles via Controlled Hydrolysis and Condensation of Silicon AlkoxideChemistry of Materials, 21
-
Damien Cartigny, Kurt Püntener, T. Ayad, M. Scalone, V. Ratovelomanana-Vidal (2010)
Highly diastereo- and enantioselective synthesis of monodifferentiated syn-1,2-diol derivatives through asymmetric transfer hydrogenation via dynamic kinetic resolution.Organic letters, 12 17
-
T. Ikariya, A. Blacker (2007)
Asymmetric transfer hydrogenation of ketones with bifunctional transition metal-based molecular catalysts.Accounts of chemical research, 40 12
-
Jianmin Mao, David Baker (1999)
A chiral rhodium complex for rapid asymmetric transfer hydrogenation of imines with high enantioselectivity.Organic letters, 1 6
-
Yun Wu, Zhicong Geng, J. Bai, Ya-wen Zhang (2011)
Synthesis of Chiral 2‐Aroyl‐1‐tetralols: Asymmetric Transfer Hydrgenation of 2‐Aroyl‐1‐tetralones via Dynamic Kinetic ResolutionChinese Journal of Chemistry, 29
-
P. Liu, P. Gu, Fei Wang, Y. Tu (2004)
Efficient heterogeneous asymmetric transfer hydrogenation of ketones using highly recyclable and accessible silica-immobilized Ru-TsDPEN catalysts.Organic letters, 6 2
-
Zhe Gao, I. Zharov (2014)
Large Pore Mesoporous Silica Nanoparticles by Templating with a Nonsurfactant Molecule, Tannic AcidChemistry of Materials, 26
-
A. Ros, Antonio Magriz, H. Dietrich, J. Lassaletta, R. Fernández (2007)
Stereoselective synthesis of syn β-hydroxy cycloalkane carboxylates: transfer hydrogenation of cyclic β-keto esters via dynamic kinetic resolutionTetrahedron, 63
-
Minghong Wang, Zhenkun Sun, Qin Yue, Jie Yang, Xiqing Wang, Yonghui Deng, Chengzhong Yu, Dongyuan Zhao (2014)
An interface-directed coassembly approach to synthesize uniform large-pore mesoporous silica spheres.Journal of the American Chemical Society, 136 5
-
M. Bartók (2010)
Unexpected inversions in asymmetric reactions: reactions with chiral metal complexes, chiral organocatalysts, and heterogeneous chiral catalysts.Chemical reviews, 110 3
-
B. Seashore-Ludlow, P. Villo, P. Somfai (2012)
Enantioselective synthesis of anti-β-hydroxy-α-amido esters by asymmetric transfer hydrogenation in emulsions.Chemistry, 18 23
-
G. Kumaraswamy, Akula Murthy, Vykunthapu Narayanarao, S. Vemulapalli, J. Bharatam (2013)
Enantioselective synthesis of δ-/γ-alkoxy-β-hydroxy-α-alkyl-substituted Weinreb amides via DKR-ATH: application to the synthesis of advanced intermediate of (-)-brevisamide.Organic & biomolecular chemistry, 11 39
-
D. Vos, M. Dams, B. Sels, P. Jacobs (2002)
Ordered mesoporous and microporous molecular sieves functionalized with transition metal complexes as catalysts for selective organic transformations.Chemical reviews, 102 10
-
K. Steward, M. Corbett, C. Goodman, Jeffrey Johnson (2012)
Asymmetric synthesis of diverse glycolic acid scaffolds via dynamic kinetic resolution of α-keto esters.Journal of the American Chemical Society, 134 49
-
D. Phan, Byoungmoo Kim, V. Dong (2009)
Phthalides by rhodium-catalyzed ketone hydroacylation.Journal of the American Chemical Society, 131 43
-
Fei Gao, Ronghua Jin, Dacheng Zhang, Quanxi Liang, Q. Ye, Guohua Liu (2013)
Flower-like mesoporous silica: a bifunctionalized catalyst for rhodium-catalyzed asymmetric transfer hydrogenation of aromatic ketones in aqueous mediumGreen Chemistry, 15
-
A. Corma, M. Domine, J. Gaona, J. Jordá, M. Navarro, F. Rey, J. Pérez-Pariente, J. Tsuji, B. Mcculloch, L. Nemeth (1998)
Strategies to improve the epoxidation activity and selectivity of Ti-MCM-41Chemical Communications
-
Rui Liu, Tanyu Cheng, Lingyu Kong, Chen Chen, Guohua Liu, Hexing Li (2013)
Highly recoverable organoruthenium-functionalized mesoporous silica boosts aqueous asymmetric transfer hydrogenation reactionJournal of Catalysis, 307
-
K. Steward, Emily Gentry, Jeffrey Johnson (2012)
Dynamic kinetic resolution of α-keto esters via asymmetric transfer hydrogenation.Journal of the American Chemical Society, 134 17
-
Hengquan Yang, Lei Zhang, Lin Zhong, Qihua Yang, Can Li (2007)
Enhanced cooperative activation effect in the hydrolytic kinetic resolution of epoxides on [Co(salen)] catalysts confined in nanocages.Angewandte Chemie, 46 36
-
Yanhang Ma, Lei Xing, Haoquan Zheng, S. Che (2011)
Anionic-cationic switchable amphoteric monodisperse mesoporous silica nanoparticles.Langmuir : the ACS journal of surfaces and colloids, 27 2
-
Akio Fujii, S. Hashiguchi, N. Uematsu, and Ikariya, R. Noyori (1996)
Ruthenium(II)-Catalyzed Asymmetric Transfer Hydrogenation of Ketones Using a Formic Acid−Triethylamine MixtureJournal of the American Chemical Society, 118
-
R. Malacea, R. Poli, E. Manoury (2010)
Asymmetric hydrosilylation, transfer hydrogenation and hydrogenation of ketones catalyzed by iridium complexesCoordination Chemistry Reviews, 254
-
Fangqiong Tang, Linlin Li, Dong Chen (2012)
Mesoporous Silica Nanoparticles: Synthesis, Biocompatibility and Drug DeliveryAdvanced Materials, 24
-
Min Wang, Feng Wang, Jiping Ma, Chen Chen, S. Shi, Jie Xu (2013)
Insights into support wettability in tuning catalytic performance in the oxidation of aliphatic alcohols to acids.Chemical communications, 49 59
-
Hengquan Yang, Xuan Jiao, Shuru Li (2012)
Hydrophobic core-hydrophilic shell-structured catalysts: a general strategy for improving the reaction rate in water.Chemical communications, 48 91
-
W. Yoo, A. Stein (2011)
Solvent Effects on Morphologies of Mesoporous Silica Spheres Prepared by Pseudomorphic TransformationsChemistry of Materials, 23
-
Aidan Hayes, D. Morris, G. Clarkson, M. Wills (2005)
A class of ruthenium(II) catalyst for asymmetric transfer hydrogenations of ketones.Journal of the American Chemical Society, 127 20
-
S. Son, Hyeon-Kyu Lee (2014)
Dynamic kinetic resolution based asymmetric transfer hydrogenation of α-alkoxy-β-ketophosphonates. Diastereo- and enantioselective synthesis of monoprotected 1,2-dihydroxyphosphonates.The Journal of organic chemistry, 79 6
-
Jinyu Wang, Liang Wu, Xiaoying Hu, Rui Liu, Ronghua Jin, Guohua Liu (2017)
One-pot synthesis of optically pure β-hydroxy sulfones via a heterogeneous ruthenium/diamine-promoted nucleophilic substitution-asymmetric transfer hydrogenation tandem processCatalysis Science & Technology, 7
-
S. Murphy, V. Dong (2013)
Enantioselective ketone hydroacylation using Noyori's transfer hydrogenation catalyst.Journal of the American Chemical Society, 135 15
-
Xiaofeng Wu, Xiaoguang Li, W. Hems, F. King, Jianliang Xiao (2004)
Accelerated asymmetric transfer hydrogenation of aromatic ketones in water.Organic & biomolecular chemistry, 2 13
-
Jun Xiong, Wenshuai Zhu, Wenjin Ding, Lei Yang, Ming Zhang, Wei Jiang, Zhen Zhao, Hua-ming Li (2015)
Hydrophobic mesoporous silica-supported heteropolyacid induced by ionic liquid as a high efficiency catalyst for the oxidative desulfurization of fuelRSC Advances, 5
-
Cheng Chen, Jie Xu, Qiaohong Zhang, Yinfa Ma, Lipeng Zhou, Min Wang (2011)
Superhydrophobic materials as efficient catalysts for hydrocarbon selective oxidation.Chemical communications, 47 4
-
Chenguang Yu, Jing He (2012)
Synergic catalytic effects in confined spaces.Chemical communications, 48 41
-
H. Shintaku, K. Nakajima, M. Kitano, M. Hara (2014)
Efficient Mukaiyama aldol reaction in water with TiO4 tetrahedra on a hydrophobic mesoporous silica surface.Chemical communications, 50 88
-
Meng Wu, Lingyu Kong, Kaiwen Wang, Ronghua Jin, Tanyu Cheng, Guohua Liu (2015)
Enantioselective 1,2-reductions of β-trifluoromethylated-α,β-unsaturated ketones to chiral allylic alcohols over organoruthenium-functionalized mesoporous silica nanospheresCatalysis Science & Technology, 5
-
S. Minakata, M. Komatsu (2009)
Organic reactions on silica in water.Chemical reviews, 109 2
-
K. Ding, Y. Uozumi (2008)
Handbook of Asymmetric Heterogeneous Catalysis -
S. Shi, Min Wang, Chen Chen, Jin Gao, Hong Ma, Jiping Ma, Jie Xu (2013)
Super-hydrophobic yolk-shell nanostructure with enhanced catalytic performance in the reduction of hydrophobic nitroaromatic compounds.Chemical communications, 49 83
-
M. Stébé, Mélanie Emo, A. Follotec, Léa Metlas-Komunjer, I. Pezron, J. Blin (2013)
Triblock siloxane copolymer surfactant: template for spherical mesoporous silica with a hexagonal pore ordering.Langmuir : the ACS journal of surfaces and colloids, 29 5
-
S. Hashiguchi, Akio Fujii, J. Takehara, T. Ikariya, R. Noyori (1995)
Asymmetric Transfer Hydrogenation of Aromatic Ketones Catalyzed by Chiral Ruthenium(II) ComplexesJournal of the American Chemical Society, 117
-
J. Thomas, R. Raja (2008)
Exploiting nanospace for asymmetric catalysis: confinement of immobilized, single-site chiral catalysts enhances enantioselectivity.Accounts of chemical research, 41 6
-
Zhuqing Liu, C. Shultz, Candice Sherwood, Shane Krska, P. Dormer, Richard Desmond, Claire Lee, E. Sherer, J. Shpungin, James Cuff, Feng Xu (2011)
Highly enantioselective synthesis of anti aryl β-hydroxy α-amino esters via DKR transfer hydrogenationTetrahedron Letters, 52
-
F. Eustache, P. Dalko, J. Cossy (2002)
Enantioselective monoreduction of 2-alkyl-1,3-diketones mediated by chiral ruthenium catalysts. dynamic kinetic resolution.Organic letters, 4 8
-
Can Li, Huidong Zhang, D. Jiang, Qihua Yang (2007)
Chiral catalysis in nanopores of mesoporous materials.Chemical communications, 6
-
T. Blasco, M. Camblor, A. Corma, P. Esteve, J. Guil, Angel Martı́nez, J. Perdigón-Melón, S. Valencia (1998)
Direct Synthesis and Characterization of Hydrophobic Aluminum-Free Ti−Beta ZeoliteJournal of Physical Chemistry B, 102
-
Juzeng An, Tanyu Cheng, Xinzhong Xiong, Liang Wu, B. Han, Guohua Liu (2016)
Yolk–shell-structured mesoporous silica: a bifunctional catalyst for nitroaldol–Michael one-pot cascade reactionCatalysis Science & Technology, 6
-
Bo Zhang, Ming‐Hua Xu, G. Lin (2009)
Catalytic enantioselective synthesis of chiral phthalides by efficient reductive cyclization of 2-acylarylcarboxylates under aqueous transfer hydrogenation conditions.Organic letters, 11 20
-
Huaisheng Zhang, Ronghua Jin, Hui Yao, Shuang Tang, Jinglan Zhuang, Guohua Liu, Hexing Li (2012)
Core-shell structured mesoporous silica: a new immobilized strategy for rhodium catalyzed asymmetric transfer hydrogenation.Chemical communications, 48 63
-
J. Limanto, Shane Krska, B. Dorner, Enrique Vazquez, Naoki Yoshikawa, L. Tan (2010)
Dynamic kinetic resolution: asymmetric transfer hydrogenation of alpha-alkyl-substituted beta-ketoamides.Organic letters, 12 3
-
Kun Zhang, Lang Xu, Jinzhu Jiang, Nathalie Calin, K. Lam, San-Jun Zhang, Haizhi Wu, Guang-Dong Wu, B. Albela, L. Bonneviot, Peng Wu (2013)
Facile large-scale synthesis of monodisperse mesoporous silica nanospheres with tunable pore structure.Journal of the American Chemical Society, 135 7
-
M. Camblor, A. Corma, P. Esteve, Ana Martínez, S. Valencia (1997)
Epoxidation of unsaturated fatty esters over large-poreTi-containing molecular sieves as catalysts: important role of thehydrophobic–hydrophilic properties of the molecular sieveChemical Communications
-
A. Mehdi, C. Reyé, R. Corriu (2011)
From molecular chemistry to hybrid nanomaterials. Design and functionalization.Chemical Society reviews, 40 2
-
S. Son, Hyeon-Kyu Lee (2013)
Dynamic kinetic resolution-based asymmetric transfer hydrogenation of 2-benzoylmorpholinones and its use in concise stereoselective synthesis of all four stereoisomers of the antidepressant reboxetine.The Journal of organic chemistry, 78 17
- Publisher
- Royal Society of Chemistry
- Copyright
- This journal is © The Royal Society of Chemistry
- ISSN
- 2044-4753
- eISSN
- 2044-4761
- DOI
- 10.1039/c8cy00648b
- Publisher site
- See Article on Publisher Site
Abstract
Immobilization of molecular catalysts in a superhydrophobic material can efficiently overcome the shortage of low catalytic efficiency in heterogeneous catalysis. In this study, by taking advantage of a superhydrophobic mesostructured silica as a support, we incorporated conveniently chiral diamine to the silicate network, thus constructing two hydrophobic rhodium/diamine- and ruthenium/diamine-functionalized heterogeneous catalysts. Analyses via solid-state carbon NMR spectroscopy disclosed the well-defined single-site active species in the silicate framework of these catalysts, while the water contact angle measurements reflected their high hydrophobicity. Characterizations via scanning and transmission electron microscopy revealed their monodispersed feature. As presented in the study, the hydrophobic rhodium/diamine-functionalized catalyst greatly promotes the enantioselective tandem reduction/lactonization of ethyl 2-acylarylcarboxylates to afford various chiral phthalides, whereas the hydrophobic ruthenium/diamine-functionalized catalyst boosts an efficient asymmetric transfer hydrogenation-dynamic kinetic resolution process for construction of 1,2-distereocentered diethyl α-benzoyl-β-hydroxyphosphonates. As envisaged, the as-made catalysts with high hydrophobicity and uniformly distributed single-site catalytically active nature make combinational contributions to their catalytic performances, affording chiral products in high yields with up to 99% enantioselectivity. Moreover, the catalysts can be also recovered easily and recycled repeatedly, making them attracting candidates in efficient organic transformations.
Journal
Catalysis Science & Technology – Royal Society of Chemistry
Published: Jun 5, 2018