Synthesis of indolizines through aldehyde-amine-alkyne couplings using metal-organic framework Cu-MOF-74 as an efficient heterogeneous catalyst

Journal of Catalysis

Volumn 337, Issue , 2016, Pages 167-176

  Dang, Giao H ^a   Lam, Huy Q ^a   Nguyen, Anh T ^a   Le, Dung T ^a   Truong, Thanh ^a   Phan, Nam T S ^a  

^a VIETNAM NATIONAL UNIVERSITY   (Viet Nam)

Author keywords

Coupling; Cu MOF 74; Heterogeneous catalyst; Indolizines; Metal organic framework

Indexed keywords

ALDEHYDES; CATALYSTS; COPPER; COUPLINGS; CRYSTALLINE MATERIALS; ELECTRON MICROSCOPY; HIGH RESOLUTION TRANSMISSION ELECTRON MICROSCOPY; HYDROCARBONS; JAVA PROGRAMMING LANGUAGE; ORGANOMETALLICS; SCANNING ELECTRON MICROSCOPY; THERMOGRAVIMETRIC ANALYSIS; TRANSMISSION ELECTRON MICROSCOPY; X RAY POWDER DIFFRACTION;

ALKYNE COUPLING; ATOMIC ABSORPTION SPECTROPHOTOMETRY; FOURIER TRANSFORM INFRARED; HETEROGENEOUS CATALYST; INDOLIZINES; METAL ORGANIC FRAMEWORK; NITROGEN PHYSISORPTION MEASUREMENTS; THREE-COMPONENT COUPLING;

CATALYST ACTIVITY;

EID: 84959010413     PISSN: 00219517     EISSN: 10902694     Source Type: Journal    
DOI: 10.1016/j.jcat.2016.02.013     Document Type: Article

References (99)

1. J. Brioche, C. Meyer, and J. Cossy Org. Lett. 17 2015 2800 2803
2. L. Xiang, Y. Yang, X. Zhou, X. Liu, X. Li, X. Kang, R. Yan, and G. Huang J. Org. Chem. 79 2014 10641 10647
3. J.B. Xia, and S.L. You Org. Lett. 11 2009 1187 1190
4. B.V.M. Teodoro, J.T.M. Correia, and F. Coelho J. Org. Chem. 80 2015 2529 2538
5. C. Wang, H. Hu, J. Xu, and W. Kan RSC Adv. 5 2015 41255 41258
6. L. Xiang, F. Zhang, B. Chen, X. Pang, X. Yang, G. Huang, and R. Yan RSC Adv. 5 2015 29424 29427
7. H. Hu, J. Feng, Y. Zhu, N. Gu, and Y. Kan RSC Adv. 2 2012 8637 8644
8. A.R. Katritzky, G. Qiu, B. Yang, and H.-Y. He J. Org. Chem. 64 1999 7618 7621
9. Y. Yang, C. Xie, Y. Xie, and Y. Zhang Org. Lett. 14 2012 957 959
10. V. Helan, A.V. Gulevich, and V. Gevorgyan Chem. Sci. 6 2015 1928 1931
11. L. Zhang, X. Li, Y. Liu, and D. Zhang Chem. Commun. 51 2015 6333 6336
12. E.J. Choi, and S.B. Park Org. Biomol. Chem. 13 2015 5202 5208
13. Z. Li, D. Chernyak, and V. Gevorgyan Org. Lett. 14 2012 6056 6059
14. A.N. Pandya, J.T. Fletcher, E.M. Villa, and D.K. Agrawal Tetrahedron Lett. 55 2014 6922 6924
15. Y. Bai, J. Zeng, J. Ma, B.K. Gorityala, and X.-W. Liu J. Comb. Chem. 12 2010 696 699
16. B. Yan, and Y. Liu Org. Lett. 9 2007 4323 4326
17. X. Wang, S.-Y. Li, Y.-M. Pan, H.-S. Wang, H. Liang, Z.-F. Chen, and X.-H. Qin Org. Lett. 16 2014 580 583
18. M.J. Albaladejo, F. Alonso, and M.J. González-Soria ACS Catal. 5 2015 3446 3456
19. H.K. Chae, D.Y. Siberio-Perez, J. Kim, Y. Go, M. Eddaoudi, A.J. Matzger, M. O'Keeffe, and O.M. Yaghi Nature 427 2004 523 527
20. D.J. Tranchemontagne, M.O.k.Z. Ni, and O.M. Yaghi Angew. Chem. Int. Ed. 47 2008 5136 5147
21. S.S. Kaye, A. Dailly, O.M. Yaghi, and J.R. Long J. Am. Chem. Soc. 129 2007 14176 14177
22. H. Furukawa, N. Ko, Y.B. Go, N. Aratani, S.B. Choi, E. Choi, A.O. Yazaydin, R.Q. Snurr, M. O'Keeffe, J. Kim, and O.M. Yaghi Science 239 2010 424 428
23. P. Horcajada, T. Chalati, C. Serre, B. Gillet, C. Sebrie, T. Baati, J.F. Eubank, D. Heurtaux, P. Clayette, C. Kreuz, J.S. Chang, Y.K. Hwang, V. Marsaud, P.N. Bories, L. Cynober, S. Gil, G. Férey, P. Couvreur, and R. Gref Nat. Mater. 9 2010 172 178
24. R.J. Kuppler, D.J. Timmons, Q.-R. Fang, J.-R. Li, T.A. Makal, M.D. Young, D. Yuan, D. Zhao, W. Zhuang, and H.-C. Zhou Coord. Chem. Rev. 253 2009 3042 3066
25. L. Ma, and W. Lin Top. Curr. Chem. 293 2010 175 205
26. H. Li, M. Eddaoudi, M. O'Keeffe, and O.M. Yaghi Nature 402 1999 276 279
27. J.L.C. Rowsell, and O.M. Yaghi Micropor. Mesopor. Mater. 73 2004 3 14
28. Z.-Q. Li, L.-G. Qiu, T. Xu, Y. Wu, W. Wang, Z.-Y. Wu, and X. Jiang Mater. Lett. 63 2009 78 80
29. B. Chen, S. Xiang, and G. Qian Acc. Chem. Res. 43 2010 1115 1124
30. D.T. Genna, A.G. Wong-Foy, A.J. Matzger, and M.S. Sanford J. Am. Chem. Soc. 135 2013 10586 10589
31. J.A. Mason, M. Veenstra, and J.R. Long Chem. Sci. 5 2014 32 51
32. M.-L. Ma, C. Ji, and S.-Q. Zang Dalton Trans. 42 2013 10579 10586
33. N.W.C. Jusoh, A.A. Jalil, S. Triwahyono, and C.R. Mamat Appl. Catal. A Gen. 492 2015 169 176
34. M. Babazadeh, R. Hosseinzadeh-Khanmiri, J. Abolhasani, E. Ghorbani-Kalhor, and A. Hassanpour RSC Adv. 5 2015 19884 19892
35. N.T.S. Phan, T.T. Nguyen, Q.H. Luu, and L.T.L. Nguyen J. Mol. Catal. A Chem. 363-364 2012 178 185
36. Z.-Y. Gu, J. Park, A. Raiff, Z. Wei, and H.-C. Zhou ChemCatChem 6 2014 67 75
37. P. Valvekens, F. Vermoortelea, and D.D. Vos Catal. Sci. Technol. 3 2013 1435 1445
38. J. Liu, L. Chen, H. Cui, J. Zhang, L. Zhang, and C.-Y. Su Chem. Soc. Rev. 43 2014 6011 6061
39. A. Corma, H. García, and F.X. Llabrés i Xamena Chem. Rev. 110 2010 4606 4655
40. A. Dhakshinamoorthy, and H. Garcia Chem. Soc. Rev. 41 2012 5262 5284
41. M. Yoon, R. Srirambalaji, and K. Kim Chem. Rev. 112 2012 1196 1231
42. F. Zadehahmadi, S. Tangestaninejad, M. Moghadam, V. Mirkhani, I. Mohammadpoor-Baltork, A.R. Khosropour, and R. Kardanpour Appl. Catal. A Gen. 477 2014 34 41
43. T. Otto, N.N. Jarenwattananon, S. Glöggler, J.W. Brown, A. Melkonian, Y.N. Ertas, and L.-S. Bouchard Appl. Catal. A Gen. 488 2014 248 255
44. Q.-X. Luo, X.-D. Song, M. Ji, S.-E. Park, C. Hao, and Y.-Q. Li Appl. Catal. A Gen. 478 2014 81 90
45. K. Leus, Y.-Y. Liu, M. Meledina, S. Turner, G.V. Tendeloo, and P.V.D. Voort J. Catal. 316 2014 201 209
46. A. Dhakshinamoorthy, A.M. Asiri, and H. Garcia Chem. Soc. Rev. 44 2015 1922 1947
47. A.H. Chughtai, N. Ahmad, H.A. Younus, A. Laypkov, F. Verpoor, Chem. Soc. Rev., 2015, in press, doi: http://dx.doi.org/10.1039/C1034CS00395K.
48. P. Wu, C. He, J. Wang, X. Peng, X. Li, Y. An, and C. Duan J. Am. Chem. Soc. 134 2012 14991 14999
49. A.S. Roy, J. Mondal, B. Banerjee, P. Mondal, A. Bhaumik, and S.M. Islam Appl. Catal. A: Gen. 469 2014 320 327
50. N.T.S. Phan, T.T. Nguyen, P. Ho, and K.D. Nguyen ChemCatChem 5 2013 1822 1831
51. T. Truong, V.T. Nguyen, H.T.X. Le, and N.T.S. Phan RSC Adv. 4 2014 52307 52315
52. Y. Luan, N. Zheng, Y. Qi, J. Tang, and G. Wang Catal. Sci. Technol. 4 2014 925 929
53. G. Yu, J. Sun, F. Muhammad, P. Wang, and G. Zhu RSC Adv. 4 2014 38804 38811
54. Y.-R. Lee, Y.-M. Chung, and W.-S. Ahn RSC Adv. 4 2014 23064 23067
55. A.S. Roy, J. Mondal, B. Banerjee, P. Mondal, A. Bhaumik, and S.M. Islam Appl. Catal. A. Gen. 469 2014 320 327
56. G.H. Dang, D.T. Nguyen, D.T. Le, T. Truong, and N.T.S. Phan J. Mol. Catal. A: Gen. 395 2014 300 306
57. G.H. Dang, T.T. Dang, D.T. Le, T. Truong, and N.T.S. Phan J. Catal. 319 2014 258 264
58. P. Valvekens, M. Vandichel, M. Waroquier, V.V. Speybroeck, and D.D. Vos J. Catal. 317 2014 1 10
59. M. Savonnet, S. Aguado, U. Ravon, D. Bazer-Bachi, V. Lecocq, N. Bats, C. Pinel, and D. Farrusseng Green Chem. 11 2009 1729 1732
60. E. Pérez-Mayoral, Z. Musilová, B. Gil, B. Marszalek, M. Položij, P. Nachtigall, and J. Čejka Dalton Trans. 41 2012 4036 4044
61. M. Opanasenko, M. Shamzhy, and J. Čejka ChemCatChem 5 2013 1024 1031
62. N.T.S. Phan, P.H.L. Vu, and T.T. Nguyen J. Catal. 306 2013 38 46
63. O.V. Zalomaeva, A.M. Chibiryaev, K.A. Kovalenko, O.A. Kholdeeva, B.S. Balzhinimaev, and V.P. Fedin J. Catal. 298 2013 179 185
64. H.T.N. Le, T.V. Tran, N.T.S. Phan, and T. Truong Catal. Sci. Technol. 5 2015 851 859
65. I. Luz, A. Corma, and F.X.L.i. Xamena Catal. Sci. Technol. 4 2014 1829 1836
66. Tanmoy Maity, D. Saha, and S. Koner ChemCatChem 6 2014 2373 2383
67. Y. Jiang, J. Huang, M. Hunger, M. Maciejewski, and A. Baiker Catal. Sci. Technol. 5 2015 897 902
68. A. Dhakshinamoorthy, M. Alvaro, and H. Garcia Adv. Synth. Catal. 351 2009 2271 2276
69. A. Dhakshinamoorthy, M. Alvaro, and H. Garcia Adv. Synth. Catal. 352 2010 711 717
70. A. Dhakshinamoorthy, M. Alvaro, and H. Garcia Adv. Synth. Catal. 352 2010 3022 3030
71. L. Alaerts, E. Séguin, H. Poelman, F. Thibault-Starzyk, P.A. Jacobs, and D.E. De Vos Chem. Eur. J. 12 2006 7353 7363
72. I. Luz, F.X. Llabrés i Xamena, and A. Corma J. Catal. 285 2012 285 291
73. I. Luz, F.X. Llabrés i Xamena, and A. Corma J. Catal. 276 2010 134 140
74. D. Ruano, M. Díaz-García, A. Alfayate, and M. Sánchez-Sánchez ChemCatChem 7 2015 674 681
75. R. Sanz, F. Martínez, G. Orcajo, L. Wojtas, and D. Briones Dalton Trans. 42 2013 2392 2398
76. G. Langhendries, D.E.D. Vos, G.V. Baron, and P.A. Jacobs J. Catal. 187 1997 453 463
77. N.T.S. Phan, and C.W. Jones J. Mol. Catal. A: Chem. 253 2006 123 131
78. H. Wang, and M. Frenklach Combust. Flame 96 1994 163 170
79. J. Jae, G.A. Tompsett, A.J. Foster, K.D. Hammond, S.M. Auerbach, R.F. Lobo, and G.W. Huber J. Catal. 279 2011 257 268
80. Y. Kubota, M. Takata, R. Matsuda, R. Kitaura, S. Kitagawa, and T.C. Kobayashi Angew. Chem. Int. Ed. 45 2006 4932 4936
81. R. Bai, G. Zhang, H. Yi, Z. Huang, X. Qi, C. Liu, J.T. Miller, A.J. Kropf, E.E. Bunel, Y. Lan, and A. Lei J. Am. Chem. Soc. 136 2014 16760 16763
82. M. Maes, S. Schouteden, K. Hirai, S. Furukawa, S. Kitagawa, and D.E. De Vos Langmuir 27 2011 9083 9087
83. S.S.-Y. Chui, S.M.-F. Lo, J.P.J. Charmant, A.G. Orpen, and L.D. William Science 1999 1148 1150
84. J. Liu, B. Lukose, O. Shekhah, H.K. Arslan, P. Weidler, H. Gliemann, S. Bräse, S. Grosjean, A. Godt, X. Feng, K. Müllen, I.-B. Magdau, T. Heine, and C. Wöll Sci. Reports 2 2012 921
85. C.G. Carson, K. Hardcastle, J. Schwartz, X. Liu, C. Hoffmann, R.A. Gerhardt, and R. Tannenbaum Eur. J. Inorg. Chem. 2009 2338 2343
86. A.N. Mlinar, B.K. Keitz, E.D. Gygi, D. Bloch, J.R. Long, and A.T. Bell ACS Catal. 4 2014
87. C. Volkringer, M. Meddouri, T. Loiseau, N. Guillou, J. Marrot, G. Férey, M. Haouas, F. Taulelle, N. Audebrand, and M. Latroche Inorg. Chem. 47 2008 11892 11901
88. J.H. Cavka, S. Jakobsen, U. Olsbye, N. Guillou, C. Lamberti, S. Bordiga, and K.P. Lillerud J. Am. Chem. Soc. 130 2008 13850 13851
89. T.G. Glover, G.W. Peterson, B.J. Schindler, D. Britt, and O.M. Yaghi Chem. Eng. Scien. 66 2011 163 170
90. L.T.L. Nguyen, T.T. Nguyen, K.D. Nguyen, and N.T.S. Phan App. Catal. A Gen. 425-426 2012 44 52
91. H. Furukawa, J. Kim, N.W. Ockwig, M. O'Keeffe, and O.M. Yaghi J. Am. Chem. Soc. 130 2008 11650 11661
92. K. Tan, N. Nijem, P. Canepa, Q. Gong, J. Li, T. Thonhauser, and Y.J. Chabal Chem. Mater. 24 2012 3153 3167
93. N.T.S. Phan, C.K. Nguyen, T.T. Nguyen, and T. Truong Catal. Sci. Technol. 4 2014 369 377
94. D. Britt, H. Furukawa, B. Wang, T.G. Glover, and O.M. Yaghi PNAS 106 2009 20637 20640
95. D. Feng, W.-C. Chung, Z. Wei, Z.-Y. Gu, H.-L. Jiang, Y.-P. Chen, D.J. Darensbourg, and H.-C. Zhou J. Am. Chem. Soc. 135 2013 17105 17110
96. D. Liu, T.-F. Liu, Y.-P. Chen, L. Zou, D. Feng, K. Wang, Q. Zhang, S. Yuan, C. Zhong, and H.-C. Zhou J. Am. Chem. Soc. 137 2015 7740 7746
97. Z. Zhang, H. Yoshikawa, and K. Awaga J. Am. Chem. Soc. 136 2014 16112 16115
98. T. Arai, N. Kawasaki, and H. Kanoh Synlett 23 2012 1549 1553
99. G.-G. Pila, M. Müller, and A. Corma Chem. Sci. 5 2014 2979 3007