메뉴 건너뛰기




Volumn 119, Issue 32, 2015, Pages 18422-18433

Impact of Deactivation Phenomena on Kinetics of the C-N Coupling Reaction over Supported Cu2O Catalysts in Continuous-Flow Conditions

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE; CATALYST ACTIVITY; CATALYST DEACTIVATION; CATALYST SELECTIVITY; COPPER OXIDES; KINETICS; REACTION KINETICS; X RAY PHOTOELECTRON SPECTROSCOPY;

EID: 84939141055     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/acs.jpcc.5b05556     Document Type: Article
Times cited : (9)

References (59)
  • 1
    • 12344337315 scopus 로고    scopus 로고
    • Palladium-Catalyzed C-N and C-O Coupling-A Practical Guide from an Industrial Vantage Point
    • Schlummer, B.; Scholz, U. Palladium-Catalyzed C-N and C-O Coupling-A Practical Guide from an Industrial Vantage Point Adv. Synth. Catal. 2004, 346, 1599-1626 10.1002/adsc.200404216
    • (2004) Adv. Synth. Catal. , vol.346 , pp. 1599-1626
    • Schlummer, B.1    Scholz, U.2
  • 2
    • 73449103586 scopus 로고    scopus 로고
    • Recent Applications of Palladium-Catalyzed Coupling Reactions in the Pharmaceutical, Agrochemical, and Fine Chemical Industries
    • Torborg, C.; Beller, M. Recent Applications of Palladium-Catalyzed Coupling Reactions in the Pharmaceutical, Agrochemical, and Fine Chemical Industries Adv. Synth. Catal. 2009, 351, 3027-3043 10.1002/adsc.200900587
    • (2009) Adv. Synth. Catal. , vol.351 , pp. 3027-3043
    • Torborg, C.1    Beller, M.2
  • 3
    • 33747071481 scopus 로고    scopus 로고
    • Selected Patented Cross-Coupling Reaction Technologies
    • Corbet, J.-P.; Mignani, G. Selected Patented Cross-Coupling Reaction Technologies Chem. Rev. 2006, 106, 2651-2710 10.1021/cr0505268
    • (2006) Chem. Rev. , vol.106 , pp. 2651-2710
    • Corbet, J.-P.1    Mignani, G.2
  • 4
    • 37049029990 scopus 로고    scopus 로고
    • Applicability of a Fiber-Supported Catalyst on a Buchwald-Hartwig Amination Reaction
    • Christensen, H.; Kiil, S.; Dam-Johansen, K.; Nielsen, O. Applicability of a Fiber-Supported Catalyst on a Buchwald-Hartwig Amination Reaction Org. Process Res. Dev. 2007, 11, 956-965 10.1021/op7000996
    • (2007) Org. Process Res. Dev. , vol.11 , pp. 956-965
    • Christensen, H.1    Kiil, S.2    Dam-Johansen, K.3    Nielsen, O.4
  • 5
    • 84905046579 scopus 로고    scopus 로고
    • The Facet-Dependent Enhanced Catalytic Activity of Pd Nanocrystals
    • Kim, M.; Kim, Y.; Hong, J. W.; Ahn, S.; Kim, W. Y.; Han, S. W. The Facet-Dependent Enhanced Catalytic Activity of Pd Nanocrystals Chem. Commun. 2014, 50, 9454-9457 10.1039/C4CC02494J
    • (2014) Chem. Commun. , vol.50 , pp. 9454-9457
    • Kim, M.1    Kim, Y.2    Hong, J.W.3    Ahn, S.4    Kim, W.Y.5    Han, S.W.6
  • 6
    • 84937574452 scopus 로고    scopus 로고
    • Precious Metals in Automotive Technology: An Unsolvable Depletion Problem ?
    • Bardi, U.; Caporali, S. Precious Metals in Automotive Technology: An Unsolvable Depletion Problem ? Minerals 2014, 4, 388-398 10.3390/min4020388
    • (2014) Minerals , vol.4 , pp. 388-398
    • Bardi, U.1    Caporali, S.2
  • 7
    • 57149139029 scopus 로고    scopus 로고
    • Synthesis of Diarylamines Catalyzed by Iron Salts
    • Correa, A.; Carril, M.; Bolm, C. Synthesis of Diarylamines Catalyzed by Iron Salts Chem.-Eur. J. 2008, 14, 10919-10922 10.1002/chem.200802018
    • (2008) Chem. - Eur. J. , vol.14 , pp. 10919-10922
    • Correa, A.1    Carril, M.2    Bolm, C.3
  • 8
    • 44349112602 scopus 로고    scopus 로고
    • Iron-Catalyzed N-Arylations of Amides
    • Correa, A.; Elmore, S.; Bolm, C. Iron-Catalyzed N-Arylations of Amides Chem.-Eur. J. 2008, 14, 3527-3529 10.1002/chem.200800293
    • (2008) Chem. - Eur. J. , vol.14 , pp. 3527-3529
    • Correa, A.1    Elmore, S.2    Bolm, C.3
  • 9
    • 13444263825 scopus 로고    scopus 로고
    • Catalysts for Cross-Coupling Reactions with Non-Activated Alkyl Halides
    • Frisch, A. C.; Beller, M. Catalysts for Cross-Coupling Reactions with Non-Activated Alkyl Halides Angew. Chem., Int. Ed. 2005, 44, 674-688 10.1002/anie.200461432
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 674-688
    • Frisch, A.C.1    Beller, M.2
  • 10
    • 0345708168 scopus 로고    scopus 로고
    • Modern Synthetic Methods for Copper-Mediated C(aryl)-O, C(aryl)-N, and C(aryl)-S Bond Formation
    • Ley, S. V.; Thomas, A. W. Modern Synthetic Methods for Copper-Mediated C(aryl)-O, C(aryl)-N, and C(aryl)-S Bond Formation Angew. Chem., Int. Ed. 2003, 42, 5400-5449 10.1002/anie.200300594
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 5400-5449
    • Ley, S.V.1    Thomas, A.W.2
  • 11
    • 47749142816 scopus 로고    scopus 로고
    • Catalytic C-C, C-N, and C-O Ullmann-Type Coupling Reactions: Copper Makes a Difference
    • Monnier, F.; Taillefer, M. Catalytic C-C, C-N, and C-O Ullmann-Type Coupling Reactions: Copper Makes a Difference Angew. Chem., Int. Ed. 2008, 47, 3096-3099 10.1002/anie.200703209
    • (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 3096-3099
    • Monnier, F.1    Taillefer, M.2
  • 12
    • 70349786460 scopus 로고    scopus 로고
    • Catalytic C-C, C-N, and C-O Ullmann-Type Coupling Reactions
    • Monnier, F.; Taillefer, M. Catalytic C-C, C-N, and C-O Ullmann-Type Coupling Reactions Angew. Chem., Int. Ed. 2009, 48, 6954-6971 10.1002/anie.200804497
    • (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 6954-6971
    • Monnier, F.1    Taillefer, M.2
  • 13
    • 46849092613 scopus 로고    scopus 로고
    • Pyrrole-2-Carboxylic Acid as a Ligand for the Cu-Catalyzed Reactions of Primary Anilines with Aryl Halides
    • Altman, R. A.; Anderson, K. W.; Buchwald, S. L. Pyrrole-2-Carboxylic Acid as a Ligand for the Cu-Catalyzed Reactions of Primary Anilines with Aryl Halides J. Org. Chem. 2008, 73, 5167-5169 10.1021/jo8008676
    • (2008) J. Org. Chem. , vol.73 , pp. 5167-5169
    • Altman, R.A.1    Anderson, K.W.2    Buchwald, S.L.3
  • 14
    • 33846689629 scopus 로고    scopus 로고
    • Efficient Iron/Copper Co-Catalyzed Arylation of Nitrogen Nucleophiles
    • Taillefer, M.; Xia, N.; Ouali, A. Efficient Iron/Copper Co-Catalyzed Arylation of Nitrogen Nucleophiles Angew. Chem., Int. Ed. 2007, 46, 934-936 10.1002/anie.200603173
    • (2007) Angew. Chem., Int. Ed. , vol.46 , pp. 934-936
    • Taillefer, M.1    Xia, N.2    Ouali, A.3
  • 16
    • 55449116748 scopus 로고    scopus 로고
    • Copper + Nickel-in-Charcoal (Cu-Ni/C): A Bimetallic, Heterogeneous Catalyst for Cross-Couplings
    • Lipshutz, B. H.; Nihan, D. M.; Vinogradova, E.; Taft, B. R.; Bošković, Ž. V. Copper + Nickel-in-Charcoal (Cu-Ni/C): A Bimetallic, Heterogeneous Catalyst for Cross-Couplings Org. Lett. 2008, 10, 4279-4282 10.1021/ol801676u
    • (2008) Org. Lett. , vol.10 , pp. 4279-4282
    • Lipshutz, B.H.1    Nihan, D.M.2    Vinogradova, E.3    Taft, B.R.4    Bošković, Ž.V.5
  • 17
    • 0033515805 scopus 로고    scopus 로고
    • An Efficient Copper-Catalyzed Coupling of Aryl Halides with Imidazoles
    • Kiyomori, A.; Marcoux, J.-F.; Buchwald, S. L. An Efficient Copper-Catalyzed Coupling of Aryl Halides with Imidazoles Tetrahedron Lett. 1999, 40, 2657-2660 10.1016/S0040-4039(99)00291-9
    • (1999) Tetrahedron Lett. , vol.40 , pp. 2657-2660
    • Kiyomori, A.1    Marcoux, J.-F.2    Buchwald, S.L.3
  • 18
    • 0037009958 scopus 로고    scopus 로고
    • The Copper-Catalyzed N-Arylation of Indoles
    • Antilla, J. C.; Klapars, A.; Buchwald, S. L. The Copper-Catalyzed N-Arylation of Indoles J. Am. Chem. Soc. 2002, 124, 11684-11688 10.1021/ja027433h
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 11684-11688
    • Antilla, J.C.1    Klapars, A.2    Buchwald, S.L.3
  • 19
    • 37549020316 scopus 로고    scopus 로고
    • Optimization of the Conditions for Copper-Mediated N-Arylation of Heteroarylamines
    • Liu, Y.; Bai, Y.; Zhang, J.; Li, Y.; Jiao, J.; Qi, X. Optimization of the Conditions for Copper-Mediated N-Arylation of Heteroarylamines Eur. J. Org. Chem. 2007, 2007, 6084-6088 10.1002/ejoc.200700577
    • (2007) Eur. J. Org. Chem. , vol.2007 , pp. 6084-6088
    • Liu, Y.1    Bai, Y.2    Zhang, J.3    Li, Y.4    Jiao, J.5    Qi, X.6
  • 20
    • 0037201095 scopus 로고    scopus 로고
    • Copper-Catalyzed Amination of Aryl Halides: Single-Step Synthesis of Triarylamines
    • Kelkar, A. A.; Patil, N. M.; Chaudhari, R. V. Copper-Catalyzed Amination of Aryl Halides: Single-Step Synthesis of Triarylamines Tetrahedron Lett. 2002, 43, 7143-7146 10.1016/S0040-4039(02)01708-2
    • (2002) Tetrahedron Lett. , vol.43 , pp. 7143-7146
    • Kelkar, A.A.1    Patil, N.M.2    Chaudhari, R.V.3
  • 21
    • 0034847422 scopus 로고    scopus 로고
    • Synthesis of SB-214857 Using Copper Catalysed Amination of Arylbromides with L-Aspartic Acid
    • Clement, J.-B.; Hayes, J. F.; Sheldrake, H. M.; Sheldrake, P. W.; Wells, A. S. Synthesis of SB-214857 Using Copper Catalysed Amination of Arylbromides with L-Aspartic Acid Synlett 2001, 2001, 1423-1427 10.1055/s-2001-16780
    • (2001) Synlett , vol.2001 , pp. 1423-1427
    • Clement, J.-B.1    Hayes, J.F.2    Sheldrake, H.M.3    Sheldrake, P.W.4    Wells, A.S.5
  • 22
    • 9244225109 scopus 로고    scopus 로고
    • Highly Efficient and Mild Copper-Catalyzed N- and C-Arylations with Aryl Bromides and Iodides
    • Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F.; Taillefer, M. Highly Efficient and Mild Copper-Catalyzed N- and C-Arylations with Aryl Bromides and Iodides Chem.-Eur. J. 2004, 10, 5607-5622 10.1002/chem.200400582
    • (2004) Chem. - Eur. J. , vol.10 , pp. 5607-5622
    • Cristau, H.-J.1    Cellier, P.P.2    Spindler, J.-F.3    Taillefer, M.4
  • 23
    • 1642479421 scopus 로고    scopus 로고
    • Mild Conditions for Copper-Catalysed N-Arylation of Pyrazoles
    • Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F.; Taillefer, M. Mild Conditions for Copper-Catalysed N-Arylation of Pyrazoles Eur. J. Org. Chem. 2004, 2004, 695-709 10.1002/ejoc.200300709
    • (2004) Eur. J. Org. Chem. , vol.2004 , pp. 695-709
    • Cristau, H.-J.1    Cellier, P.P.2    Spindler, J.-F.3    Taillefer, M.4
  • 24
    • 38049027866 scopus 로고    scopus 로고
    • Ninhydrin: An Efficient Ligand for the Cu-Catalyzed N-Arylation of Nitrogen-Containing Heterocycles with Aryl Halides
    • Huang, Y.-Z.; Gao, J.; Ma, H.; Miao, H.; Xu, J. Ninhydrin: An Efficient Ligand for the Cu-Catalyzed N-Arylation of Nitrogen-Containing Heterocycles with Aryl Halides Tetrahedron Lett. 2008, 49, 948-951 10.1016/j.tetlet.2007.12.026
    • (2008) Tetrahedron Lett. , vol.49 , pp. 948-951
    • Huang, Y.-Z.1    Gao, J.2    Ma, H.3    Miao, H.4    Xu, J.5
  • 25
    • 33746174994 scopus 로고    scopus 로고
    • 4,7-Dimethoxy-1,10-Phenanthroline: An Excellent Ligand for the Cu-Catalyzed N-Arylation of Imidazoles
    • Altman, R. A.; Buchwald, S. L. 4,7-Dimethoxy-1,10-Phenanthroline: An Excellent Ligand for the Cu-Catalyzed N-Arylation of Imidazoles Org. Lett. 2006, 8, 2779-2782 10.1021/ol0608505
    • (2006) Org. Lett. , vol.8 , pp. 2779-2782
    • Altman, R.A.1    Buchwald, S.L.2
  • 26
    • 84892579751 scopus 로고    scopus 로고
    • Magnetic Silica Supported Copper: A Modular Approach to Aqueous Ullmann-Type Amination of Aryl Halides
    • NasirBaig, R. B.; Varma, R. S. Magnetic Silica Supported Copper: A Modular Approach to Aqueous Ullmann-Type Amination of Aryl Halides RSC Adv. 2014, 4, 6568-6572 10.1039/c3ra45606d
    • (2014) RSC Adv. , vol.4 , pp. 6568-6572
    • Nasirbaig, R.B.1    Varma, R.S.2
  • 27
    • 34548152778 scopus 로고    scopus 로고
    • Novel CuO Nanoparticle Catalyzed C-N Cross Coupling of Amines with Iodobenzene
    • Rout, L.; Jammi, S.; Punniyamurthy, T. Novel CuO Nanoparticle Catalyzed C-N Cross Coupling of Amines with Iodobenzene Org. Lett. 2007, 9, 3397-3399 10.1021/ol0713887
    • (2007) Org. Lett. , vol.9 , pp. 3397-3399
    • Rout, L.1    Jammi, S.2    Punniyamurthy, T.3
  • 28
    • 34547438784 scopus 로고    scopus 로고
    • Ullmann Reaction in Tetraethyl Orthosilicate: A Novel Synthesis of Triarylamines and Diaryl Ethers
    • Zhao, Y.; Wang, Y.; Sun, H.; Li, L.; Zhang, H. Ullmann Reaction in Tetraethyl Orthosilicate: A Novel Synthesis of Triarylamines and Diaryl Ethers Chem. Commun. 2007, 30, 3186-3188 10.1039/b706449g
    • (2007) Chem. Commun. , vol.30 , pp. 3186-3188
    • Zhao, Y.1    Wang, Y.2    Sun, H.3    Li, L.4    Zhang, H.5
  • 29
    • 34848824382 scopus 로고    scopus 로고
    • Cu-Catalyzed Cross-Couplings under Ligandless Conditions
    • Tao, C. Z.; Li, J.; Cui, X.; Fu, Y.; Guo, Q. X. Cu-Catalyzed Cross-Couplings under Ligandless Conditions Chin. Chem. Lett. 2007, 18, 1199-1202 10.1016/j.cclet.2007.07.016
    • (2007) Chin. Chem. Lett. , vol.18 , pp. 1199-1202
    • Tao, C.Z.1    Li, J.2    Cui, X.3    Fu, Y.4    Guo, Q.X.5
  • 30
    • 84867798645 scopus 로고    scopus 로고
    • Direct N-Arylation of Azaheterocycles with Aryl Halides under Ligand-Free Condition
    • Yang, Q.; Wang, Y.; Zhang, B.; Zhang, M. Direct N-Arylation of Azaheterocycles with Aryl Halides under Ligand-Free Condition Chin. J. Chem. 2012, 30, 2389-2393 10.1002/cjoc.201100715
    • (2012) Chin. J. Chem. , vol.30 , pp. 2389-2393
    • Yang, Q.1    Wang, Y.2    Zhang, B.3    Zhang, M.4
  • 31
    • 84900872737 scopus 로고    scopus 로고
    • Ligand-Free Ullmann-Type C-Heteroatom Couplings under Practical Conditions
    • Güell, I.; Ribas, X. Ligand-Free Ullmann-Type C-Heteroatom Couplings Under Practical Conditions Eur. J. Org. Chem. 2014, 2014, 3188-3195 10.1002/ejoc.201400033
    • (2014) Eur. J. Org. Chem. , vol.2014 , pp. 3188-3195
    • Güell, I.1    Ribas, X.2
  • 32
    • 37349108522 scopus 로고    scopus 로고
    • Ligand-Free Copper-Catalyzed N-Arylation of Nitrogen Nucleophiles
    • Correa, A.; Bolm, C. Ligand-Free Copper-Catalyzed N-Arylation of Nitrogen Nucleophiles Adv. Synth. Catal. 2007, 349, 2673-2676 10.1002/adsc.200700408
    • (2007) Adv. Synth. Catal. , vol.349 , pp. 2673-2676
    • Correa, A.1    Bolm, C.2
  • 33
    • 84890031172 scopus 로고    scopus 로고
    • Ligand-Free Copper(I) Oxide Nanoparticle-Catalysed Amination of Aryl Halides in Ionic Liquids
    • Kessler, M. T.; Robke, S.; Sahler, S.; Prechtl, M. H. G. Ligand-Free Copper(I) Oxide Nanoparticle-Catalysed Amination of Aryl Halides in Ionic Liquids Catal. Sci. Technol. 2014, 4, 102-108 10.1039/C3CY00543G
    • (2014) Catal. Sci. Technol. , vol.4 , pp. 102-108
    • Kessler, M.T.1    Robke, S.2    Sahler, S.3    Prechtl, M.H.G.4
  • 34
    • 84892652046 scopus 로고    scopus 로고
    • Nano Copper(i) Oxide/zinc Oxide Catalyzed N-Arylation of Nitrogen-Containing Heterocycles with Aryl Halides and Arylboronic Acids in Air
    • Hosseini-Sarvari, M.; Moeini, F. Nano Copper(i) Oxide/zinc Oxide Catalyzed N-Arylation of Nitrogen-Containing Heterocycles with Aryl Halides and Arylboronic Acids in Air RSC Adv. 2014, 4, 7321-7329 10.1039/c3ra46548a
    • (2014) RSC Adv. , vol.4 , pp. 7321-7329
    • Hosseini-Sarvari, M.1    Moeini, F.2
  • 35
    • 34147103330 scopus 로고    scopus 로고
    • Rapid and Efficient Microwave-Assisted Copper(0)-Catalyzed Ullmann Coupling Reaction: General Access to Anilinoanthraquinone Derivatives
    • Baqi, Y.; Müller, C. E. Rapid and Efficient Microwave-Assisted Copper(0)-Catalyzed Ullmann Coupling Reaction: General Access to Anilinoanthraquinone Derivatives Org. Lett. 2007, 9, 1271-1274 10.1021/ol070102v
    • (2007) Org. Lett. , vol.9 , pp. 1271-1274
    • Baqi, Y.1    Müller, C.E.2
  • 36
    • 53849124671 scopus 로고    scopus 로고
    • Highly Practical "ligand-Free-Like" Copper-Catalyzed N-Arylation of Azoles in Lower Nitrile Solvents
    • Zhu, R.; Xing, L.; Wang, X.; Cheng, C.; Su, D.; Hu, Y. Highly Practical "Ligand-Free-Like" Copper-Catalyzed N-Arylation of Azoles in Lower Nitrile Solvents Adv. Synth. Catal. 2008, 350, 1253-1257 10.1002/adsc.200700535
    • (2008) Adv. Synth. Catal. , vol.350 , pp. 1253-1257
    • Zhu, R.1    Xing, L.2    Wang, X.3    Cheng, C.4    Su, D.5    Hu, Y.6
  • 37
    • 84949115493 scopus 로고    scopus 로고
    • Synthesis of N-Aryl Imidazoles Catalyzed by Copper Nanoparticles on Nanosized Silica-Coated Maghemite
    • Nador, F.; Volpe, M. A.; Alonso, F.; Radivoy, G. Synthesis of N-Aryl Imidazoles Catalyzed by Copper Nanoparticles on Nanosized Silica-Coated Maghemite Tetrahedron 2014, 70, 6082-6087 10.1016/j.tet.2014.04.003
    • (2014) Tetrahedron , vol.70 , pp. 6082-6087
    • Nador, F.1    Volpe, M.A.2    Alonso, F.3    Radivoy, G.4
  • 38
    • 16244411305 scopus 로고    scopus 로고
    • The Role of Chelating Diamine Ligands in the Goldberg Reaction: A Kinetic Study on the Copper-Catalyzed Amidation of Aryl Iodides
    • Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. The Role of Chelating Diamine Ligands in the Goldberg Reaction: A Kinetic Study on the Copper-Catalyzed Amidation of Aryl Iodides J. Am. Chem. Soc. 2005, 127, 4120-4121 10.1021/ja050120c
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 4120-4121
    • Strieter, E.R.1    Blackmond, D.G.2    Buchwald, S.L.3
  • 39
    • 48249117090 scopus 로고    scopus 로고
    • Copper Complexes of Anionic Nitrogen Ligands in the Amidation and Imidation of Aryl Halides
    • Tye, J. W.; Weng, Z.; Johns, A. M.; Incarvito, C. D.; Hartwig, J. F. Copper Complexes of Anionic Nitrogen Ligands in the Amidation and Imidation of Aryl Halides J. Am. Chem. Soc. 2008, 130, 9971-9983 10.1021/ja076668w
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 9971-9983
    • Tye, J.W.1    Weng, Z.2    Johns, A.M.3    Incarvito, C.D.4    Hartwig, J.F.5
  • 40
    • 47749101331 scopus 로고    scopus 로고
    • Carbon-Nitrogen Bond Formation Involving Well-Defined Aryl-Copper(III) Complexes
    • Huffman, L. M.; Stahl, S. S. Carbon-Nitrogen Bond Formation Involving Well-Defined Aryl-Copper(III) Complexes J. Am. Chem. Soc. 2008, 130, 9196-9197 10.1021/ja802123p
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 9196-9197
    • Huffman, L.M.1    Stahl, S.S.2
  • 41
    • 78649918300 scopus 로고    scopus 로고
    • Kinetic Investigation of a Ligand-Accelerated Sub-Mol % Copper-Catalyzed C-N Cross-Coupling Reaction
    • Larsson, P.-F.; Bolm, C.; Norrby, P.-O. Kinetic Investigation of a Ligand-Accelerated Sub-Mol % Copper-Catalyzed C-N Cross-Coupling Reaction Chem.-Eur. J. 2010, 16, 13613-13616 10.1002/chem.201002021
    • (2010) Chem. - Eur. J. , vol.16 , pp. 13613-13616
    • Larsson, P.-F.1    Bolm, C.2    Norrby, P.-O.3
  • 42
    • 84871387220 scopus 로고    scopus 로고
    • Homogenous Bimetallic Catalysis on Amination of ArX and ArX2 in Aqueous Medium-Synergistic Effect of Dicopper Complexes
    • Liao, B.-S.; Liu, S.-T. Homogenous Bimetallic Catalysis on Amination of ArX and ArX2 in Aqueous Medium-Synergistic Effect of Dicopper Complexes Catal. Commun. 2013, 32, 28-31 10.1016/j.catcom.2012.11.027
    • (2013) Catal. Commun. , vol.32 , pp. 28-31
    • Liao, B.-S.1    Liu, S.-T.2
  • 43
    • 34548591384 scopus 로고    scopus 로고
    • Theoretical Study on Copper(I)-Catalyzed Cross-Coupling between Aryl Halides and Amides
    • Zhang, S.-L.; Liu, L.; Fu, Y.; Guo, Q.-X. Theoretical Study on Copper(I)-Catalyzed Cross-Coupling between Aryl Halides and Amides Organometallics 2007, 26, 4546-4554 10.1021/om700573h
    • (2007) Organometallics , vol.26 , pp. 4546-4554
    • Zhang, S.-L.1    Liu, L.2    Fu, Y.3    Guo, Q.-X.4
  • 44
    • 84900295281 scopus 로고    scopus 로고
    • Mechanistic Aspects of Submol % Copper-Catalyzed C-N Cross-Coupling
    • Larsson, P.-F.; Wallentin, C.-J.; Norrby, P.-O. Mechanistic Aspects of Submol % Copper-Catalyzed C-N Cross-Coupling ChemCatChem 2014, 6, 1277-1282 10.1002/cctc.201301088
    • (2014) ChemCatChem , vol.6 , pp. 1277-1282
    • Larsson, P.-F.1    Wallentin, C.-J.2    Norrby, P.-O.3
  • 45
    • 84876318014 scopus 로고    scopus 로고
    • Palladium-N-Heterocyclic Carbene (NHC) Catalyzed C-N Bond Formation in a Continuous Flow Microreactor. Effect of Process Parameters and Comparison with Batch Operation
    • Pommella, A.; Tomaiuolo, G.; Chartoire, A.; Caserta, S.; Toscano, G.; Nolan, S. P.; Guido, S. Palladium-N-Heterocyclic Carbene (NHC) Catalyzed C-N Bond Formation in a Continuous Flow Microreactor. Effect of Process Parameters and Comparison with Batch Operation Chem. Eng. J. 2013, 223, 578-583 10.1016/j.cej.2013.03.070
    • (2013) Chem. Eng. J. , vol.223 , pp. 578-583
    • Pommella, A.1    Tomaiuolo, G.2    Chartoire, A.3    Caserta, S.4    Toscano, G.5    Nolan, S.P.6    Guido, S.7
  • 46
    • 84939137835 scopus 로고    scopus 로고
    • Introduction to Reactor Design Fundamentals for Ideal Systems
    • In; Gulf Professional Publishing: Oxford, U.K. pp; DOI.
    • Coker, A. K. Introduction to Reactor Design Fundamentals for Ideal Systems. In Modeling of Chemical Kinetics and Reactor Design; Gulf Professional Publishing: Oxford, U.K., 2001; pp 371-372; DOI: 10.1016/B978-088415481-5/50007-3.
    • (2001) Modeling of Chemical Kinetics and Reactor Design , pp. 371-372
    • Coker, A.K.1
  • 47
    • 84891384268 scopus 로고    scopus 로고
    • A Kinetic Study on the Cu(0)-Catalyzed Ullmann-Type Nucleophilic Aromatic Substitution C-O Coupling of Potassium Phenolate and 4-Chloropyridine
    • Benaskar, F.; Engels, V.; Patil, N. G.; Rebrov, E. V.; Meuldijk, J.; Hessel, V.; Hulshof, L. A.; Wheatley, A. E. H.; Schouten, J. C. A Kinetic Study on the Cu(0)-Catalyzed Ullmann-Type Nucleophilic Aromatic Substitution C-O Coupling of Potassium Phenolate and 4-Chloropyridine Ind. Eng. Chem. Res. 2013, 52, 18206-18214 10.1021/ie402956n
    • (2013) Ind. Eng. Chem. Res. , vol.52 , pp. 18206-18214
    • Benaskar, F.1    Engels, V.2    Patil, N.G.3    Rebrov, E.V.4    Meuldijk, J.5    Hessel, V.6    Hulshof, L.A.7    Wheatley, A.E.H.8    Schouten, J.C.9
  • 48
    • 84898078438 scopus 로고    scopus 로고
    • Combined Photoemission and Scanning Tunneling Microscopy Study of the Surface-Assisted Ullmann Coupling Reaction
    • Chen, M.; Xiao, J.; Steinrück, H.-P.; Wang, S.; Wang, W.; Lin, N.; Hieringer, W.; Gottfried, J. M. Combined Photoemission and Scanning Tunneling Microscopy Study of the Surface-Assisted Ullmann Coupling Reaction J. Phys. Chem. C 2014, 118, 6820-6830 10.1021/jp4121468
    • (2014) J. Phys. Chem. C , vol.118 , pp. 6820-6830
    • Chen, M.1    Xiao, J.2    Steinrück, H.-P.3    Wang, S.4    Wang, W.5    Lin, N.6    Hieringer, W.7    Gottfried, J.M.8
  • 49
    • 84903118883 scopus 로고    scopus 로고
    • Covalent, Organometallic, and Halogen-Bonded Nanomeshes from Tetrabromo-Terphenyl by Surface-Assisted Synthesis on Cu(111)
    • Fan, Q.; Wang, C.; Liu, L.; Han, Y.; Zhao, J.; Zhu, J.; Kuttner, J.; Hilt, G.; Gottfried, J. M. Covalent, Organometallic, and Halogen-Bonded Nanomeshes from Tetrabromo-Terphenyl by Surface-Assisted Synthesis on Cu(111) J. Phys. Chem. C 2014, 118, 13018-13025 10.1021/jp5037475
    • (2014) J. Phys. Chem. C , vol.118 , pp. 13018-13025
    • Fan, Q.1    Wang, C.2    Liu, L.3    Han, Y.4    Zhao, J.5    Zhu, J.6    Kuttner, J.7    Hilt, G.8    Gottfried, J.M.9
  • 52
    • 0031208312 scopus 로고    scopus 로고
    • Effect of Coexchanging with a Second Metal Upon the Interaction of Nitric Oxide with Cu-ZSM-5
    • Paîrvulescu, V. I.; Grange, P.; Delmon, B. Effect of Coexchanging with a Second Metal Upon the Interaction of Nitric Oxide with Cu-ZSM-5 J. Phys. Chem. B 1997, 101, 6933-6942 10.1021/jp971207q
    • (1997) J. Phys. Chem. B , vol.101 , pp. 6933-6942
    • Paîrvulescu, V.I.1    Grange, P.2    Delmon, B.3
  • 53
    • 0342352245 scopus 로고    scopus 로고
    • NO Decomposition over Bicomponent Cu-Sm-ZSM-5 Zeolites
    • Paîrvulescu, V. I.; Oelker, P.; Grange, P.; Delmon, B. NO Decomposition Over Bicomponent Cu-Sm-ZSM-5 Zeolites Appl. Catal., B 1998, 16, 1-17 10.1016/S0926-3373(97)00057-X
    • (1998) Appl. Catal., B , vol.16 , pp. 1-17
    • Paîrvulescu, V.I.1    Oelker, P.2    Grange, P.3    Delmon, B.4
  • 54
    • 0343090403 scopus 로고    scopus 로고
    • NO Decomposition over Cu-Sm-ZSM-5 Zeolites Containing Low-Exchanged Copper
    • Paîrvulescu, V. I.; Centeno, M. A.; Grange, P.; Delmon, B. NO Decomposition Over Cu-Sm-ZSM-5 Zeolites Containing Low-Exchanged Copper J. Catal. 2000, 191, 445-455 10.1006/jcat.2000.2818
    • (2000) J. Catal. , vol.191 , pp. 445-455
    • Paîrvulescu, V.I.1    Centeno, M.A.2    Grange, P.3    Delmon, B.4
  • 55
    • 0035840913 scopus 로고    scopus 로고
    • NO Decomposition over Physical Mixtures of Cu-ZSM-5 with Zeolites or Oxides
    • Paîrvulescu, V. I.; Grange, P.; Delmon, B. NO Decomposition Over Physical Mixtures of Cu-ZSM-5 with Zeolites or Oxides Appl. Catal., B 2001, 33, 223-237 10.1016/S0926-3373(01)00182-5
    • (2001) Appl. Catal., B , vol.33 , pp. 223-237
    • Paîrvulescu, V.I.1    Grange, P.2    Delmon, B.3
  • 58
    • 1842867924 scopus 로고    scopus 로고
    • 3 Supported Copper Oxide Catalyst
    • 3 Supported Copper Oxide Catalyst Appl. Catal., A 1996, 141, 17-29 10.1016/0926-860X(96)00049-X
    • (1996) Appl. Catal., A , vol.141 , pp. 17-29
    • Dow, W.-P.1    Huang, T.-J.2
  • 59
    • 0001251339 scopus 로고    scopus 로고
    • Yttria-Stabilized Zirconia Supported Copper Oxide Catalyst: II. Effect of Oxygen Vacancy of Support on Catalytic Activity for CO Oxidation
    • Dow, W.-P.; Huang, T.-J. Yttria-Stabilized Zirconia Supported Copper Oxide Catalyst: II. Effect of Oxygen Vacancy of Support on Catalytic Activity for CO Oxidation J. Catal. 1996, 160, 171-182 10.1006/jcat.1996.0136
    • (1996) J. Catal. , vol.160 , pp. 171-182
    • Dow, W.-P.1    Huang, T.-J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.