Metal-free and solvent-free oxidative coupling of amines to imines with mesoporous carbon from macrocyclic compounds

ACS Catalysis

Volumn 5, Issue 5, 2015, Pages 2788-2794

  Chen, Bo ^a,b   Wang, Lianyue ^a   Dai, Wen ^a   Shang, Sensen ^a,b   Lv, Ying ^a   Gao, Shuang ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

aerobic oxidation; heterogeneous catalysis; imines; mesoporous carbon; metal free

Indexed keywords

ACTIVATION ANALYSIS; AMINES; CARBON; CATALYSIS; CATALYST ACTIVITY; CATALYST SELECTIVITY; CATALYSTS; COLLOIDS; MACROMOLECULES; MOLECULAR OXYGEN; NITROGEN COMPOUNDS; SILICA; SURFACE DEFECTS;

AEROBIC OXIDATIONS; HETEROGENEOUS CATALYST; HOMOGENEOUS DISTRIBUTION; IMINES; MESOPOROUS CARBON; MESOPOROUS STRUCTURES; METAL FREE; ORDERED MESOPOROUS SILICAS;

MESOPOROUS MATERIALS;

EID: 84928941392     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/acscatal.5b00244     Document Type: Article

References (75)

1. Murahashi, S. I. Angew. Chem., Int. Ed. Engl. 1995, 34, 2443-2465 10.1002/anie.199524431
2. Kobayashi, S.; Ishitani, H. Chem. Rev. 1999, 99, 1069-1094 10.1021/cr980414z
3. He, R.; Jin, X.; Chen, H.; Huang, Z.-T.; Zheng, Q.-Y.; Wang, C. J. Am. Chem. Soc. 2014, 136, 6558-6561 10.1021/ja503520t
4. Yao, S.; Saaby, S.; Hazell, R. G.; Jørgensen, K. A. Chem.-Eur. J. 2000, 6, 2435-2448 10.1002/1521-3765(20000703)6:13<2435::AID-CHEM2435>3.0.CO;2-Z
5. Liu, Z.-Y.; Wang, Y.-M.; Li, Z.-R.; Jiang, J.-D.; Boykin, D. W. Bioorg. Med. Chem. Lett. 2009, 19, 5661-5664 10.1016/j.bmcl.2009.08.025
6. Kobayashi, S.; Mori, Y.; Fossey, J. S.; Salter, M. M. Chem. Rev. 2011, 111, 2626-2704 10.1021/cr100204f
7. Greb, L.; Lehn, J.-M. J. Am. Chem. Soc. 2014, 136, 13114-13117 10.1021/ja506034n
8. Sun, H.; Su, F. Z.; Ni, J.; Cao, Y.; He, H. Y.; Fan, K. N. Angew. Chem., Int. Ed. 2009, 48, 4390-4393 10.1002/anie.200900802
9. Gnanaprakasam, B.; Zhang, J.; Milstein, D. Angew. Chem., Int. Ed. 2010, 49, 1468-1471 10.1002/anie.200907018
10. Soulé, J.-F.; Miyamura, H.; Kobayashi, S. Chem. Commun. 2013, 49, 355-357 10.1039/C2CC36213A
11. Chen, B.; Li, J.; Dai, W.; Wang, L.; Gao, S. Green Chem. 2014, 16, 3328-3334 10.1039/c4gc00336e
12. Tamura, M.; Tomishige, K. Angew. Chem., Int. Ed. 2015, 54, 864-867 10.1002/anie.201409601
13. éll, A. H.; Samec, J. S.; Brasse, C.; Bäckvall, J.-E. Chem. Commun. 2002, 1144-1145 10.1039/b202117j
14. Yamaguchi, K.; Mizuno, N. Angew. Chem., Int. Ed. 2003, 42, 1480-1483 10.1002/anie.200250779
15. Nicolaou, K.; Mathison, C. J.; Montagnon, T. Angew. Chem., Int. Ed. 2003, 42, 4077-4082 10.1002/anie.200352076
16. Yuan, H.; Yoo, W.-J.; Miyamura, H.; Kobayashi, S. J. Am. Chem. Soc. 2012, 134, 13970-13973 10.1021/ja306934b
17. Sonobe, T.; Oisaki, K.; Kanai, M. Chem. Sci. 2012, 3, 3249-3255 10.1039/c2sc20699d
18. Yuan, B.; Chong, R.; Zhang, B.; Li, J.; Liu, Y.; Li, C. Chem. Commun. 2014, 50, 15593-15596 10.1039/C4CC07097F
19. Wu, Y.; Yuan, B.; Li, M.; Zhang, W.-H.; Liu, Y.; Li, C. Chem. Sci. 2015, 6, 1873-1878 10.1039/C4SC03229B
20. Severin, R.; Doye, S. Chem. Soc. Rev. 2007, 36, 1407-1420 10.1039/b600981f
21. Pelletier, G.; Bechara, W. S.; Charette, A. B. J. Am. Chem. Soc. 2010, 132, 12817-12819 10.1021/ja105194s
22. Cui, X.; Shi, F.; Deng, Y. Chem. Commun. 2012, 48, 7586-7588 10.1039/c2cc31438j
23. Patil, R. D.; Adimurthy, S. Asian J. Org. Chem. 2013, 2, 726-744 10.1002/ajoc.201300012
24. Largeron, M.; Fleury, M. B. Science 2013, 339, 43-44 10.1126/science.1232220
25. Furukawa, S.; Ohno, Y.; Shishido, T.; Teramura, K.; Tanaka, T. ACS Catal. 2011, 1, 1150-1153 10.1021/cs200318n
26. Lang, X.; Ji, H.; Chen, C.; Ma, W.; Zhao, J. Angew. Chem., Int. Ed. 2011, 50, 3934-3937 10.1002/anie.201007056
27. Wendlandt, A. E.; Stahl, S. S. Org. Lett. 2012, 14, 2850-2853 10.1021/ol301095j
28. Al-Hmoud, L.; Jones, C. W. J. Catal. 2013, 301, 116-124 10.1016/j.jcat.2013.01.027
29. Li, N.; Lang, X.; Ma, W.; Ji, H.; Chen, C.; Zhao, J. Chem. Commun. 2013, 49, 5034-5036 10.1039/c3cc41407h
30. Tayade, K. N.; Mishra, M. J. Mol. Catal. A: Chem. 2014, 382, 114-125 10.1016/j.molcata.2013.11.001
31. Murahashi, S.-I.; Okano, Y.; Sato, H.; Nakae, T.; Komiya, N. Synlett 2007, 2007, 1675-1678 10.1055/s-2007-984515
32. Schümperli, M. T.; Hammond, C.; Hermans, I. ACS Catal. 2012, 2, 1108-1117 10.1021/cs300212q
33. Zhu, B.; Lazar, M.; Trewyn, B. G.; Angelici, R. J. J. Catal. 2008, 260, 1-6 10.1016/j.jcat.2008.08.012
34. Grirrane, A.; Corma, A.; Garcia, H. J. Catal. 2009, 264, 138-144 10.1016/j.jcat.2009.03.015
35. So, M.-H.; Liu, Y.; Ho, C.-M.; Che, C.-M. Chem.-Asian J. 2009, 4, 1551-1561 10.1002/asia.200900261
36. Naya, S.-i.; Kimura, K.; Tada, H. ACS Catal. 2012, 3, 10-13 10.1021/cs300682d
37. Wang, J.-R.; Fu, Y.; Zhang, B.-B.; Cui, X.; Liu, L.; Guo, Q.-X. Tetrahedron Lett. 2006, 47, 8293-8297 10.1016/j.tetlet.2006.09.088
38. Furukawa, S.; Suga, A.; Komatsu, T. Chem. Commun. 2014, 50, 3277-3280 10.1039/c4cc00024b
39. Ho, H. A.; Manna, K.; Sadow, A. D. Angew. Chem., Int. Ed. 2012, 51, 8607-8610 10.1002/anie.201203556
40. Kodama, S.; Yoshida, J.; Nomoto, A.; Ueta, Y.; Yano, S.; Ueshima, M.; Ogawa, A. Tetrahedron Lett. 2010, 51, 2450-2452 10.1016/j.tetlet.2010.02.150
41. Wang, L.; Chen, B.; Ren, L.; Zhang, H.; Lü, Y.; Gao, S. Chin. J. Catal. 2015, 36, 19-23 10.1016/S1872-2067(14)60196-0
42. Patil, R. D.; Adimurthy, S. Adv. Synth. Catal. 2011, 353, 1695-1700 10.1002/adsc.201100100
43. Largeron, M.; Fleury, M. B. Angew. Chem., Int. Ed. 2012, 51, 5409-5412 10.1002/anie.201200587
44. Kang, Q.; Zhang, Y. G. Green Chem. 2012, 14, 1016-1019 10.1039/c2gc16548a
45. Dhakshinamoorthy, A.; Alvaro, M.; Garcia, H. ChemCatChem 2010, 2, 1438-1443 10.1002/cctc.201000175
46. Zhang, E. L.; Tian, H. W.; Xu, S. D.; Yu, X. C.; Xu, Q. Org. Lett. 2013, 15, 2704-2707 10.1021/ol4010118
47. Goettmann, F.; Fischer, A.; Antonietti, M.; Thomas, A. Angew. Chem., Int. Ed. 2006, 45, 4467-4471 10.1002/anie.200600412
48. Hayashi, M. Chem. Rec. 2008, 8, 252-267 10.1002/tcr.20152
49. Kuang, Y.; Islam, N. M.; Nabae, Y.; Hayakawa, T.; Kakimoto, M.-a. Angew. Chem., Int. Ed. 2010, 49, 436-440 10.1002/anie.200904362
50. Wang, Y.; Zhang, J.; Wang, X.; Antonietti, M.; Li, H. Angew. Chem., Int. Ed. 2010, 49, 3356-3359 10.1002/anie.201000120
51. Wang, Y.; Wang, X.; Antonietti, M. Angew. Chem., Int. Ed. 2012, 51, 68-89 10.1002/anie.201101182
52. Su, C.; Loh, K. P. Acc. Chem. Res. 2013, 46, 2275-2285 10.1021/ar300118v
53. Titirici, M.-M.; White, R. J.; Brun, N.; Budarin, V. L.; Su, D. S.; del Monte, F.; Clark, J. H.; MacLachlan, M. J. Chem. Soc. Rev. 2015, 44, 250-290 10.1039/C4CS00232F
54. Liang, C.; Li, Z.; Dai, S. Angew. Chem., Int. Ed. 2008, 47, 3696-3717 10.1002/anie.200702046
55. Zhang, J.; Liu, X.; Blume, R.; Zhang, A.; Schlögl, R.; Su, D. S. Science 2008, 322, 73-77 10.1126/science.1161916
56. Paraknowitsch, J. P.; Thomas, A. Energy Environ. Sci. 2013, 6, 2839-2855 10.1039/c3ee41444b
57. Huang, H.; Huang, J.; Liu, Y.-M.; He, H.-Y.; Cao, Y.; Fan, K.-N. Green Chem. 2012, 14, 930-934 10.1039/c2gc16681j
58. Su, F.; Mathew, S. C.; Möhlmann, L.; Antonietti, M.; Wang, X.; Blechert, S. Angew. Chem., Int. Ed. 2011, 50, 657-660 10.1002/anie.201004365
59. Su, C.; Acik, M.; Takai, K.; Lu, J.; Hao, S.-j.; Zheng, Y.; Wu, P.; Bao, Q.; Enoki, T.; Chabal, Y. J.; Ping Loh, K. Nat. Commun. 2012, 3, 1298 10.1038/ncomms2315
60. Li, X.-H.; Antonietti, M. Angew. Chem., Int. Ed. 2013, 52, 4572-4576 10.1002/anie.201209320
61. Wang, H.; Zheng, X.; Chen, H.; Yan, K.; Zhu, Z.; Yang, S. Chem. Commun. 2014, 50, 7517-7520 10.1039/c4cc01707b
62. Dodelet, J.-P. N4-macrocyclic metal complexes; Springer Science + Business Media: LLC: New York, 2006; p 83.
63. Ross, J. R. Heterogeneous catalysis: fundamentals and applications; Elsevier: Amsterdam: The Netherlands, 2012; p 17.
64. Rawalekar, S.; Mokari, T. Adv. Energy Mater. 2013, 3, 12-27 10.1002/aenm.201200511
65. Chi, K.-W.; Hwang, H. Y.; Park, J. Y.; Lee, C. W. Synth. Met. 2009, 159, 26-28 10.1016/j.synthmet.2008.07.009
66. Long, J.; Xie, X.; Xu, J.; Gu, Q.; Chen, L.; Wang, X. ACS Catal. 2012, 2, 622-631 10.1021/cs3000396
67. Gao, Y.; Hu, G.; Zhong, J.; Shi, Z.; Zhu, Y.; Su, D. S.; Wang, J.; Bao, X.; Ma, D. Angew. Chem., Int. Ed. 2013, 52, 2109-2113 10.1002/anie.201207918
68. Silva, R.; Voiry, D.; Chhowalla, M.; Asefa, T. J. Am. Chem. Soc. 2013, 135, 7823-7826 10.1021/ja402450a
69. Datsyuk, V.; Kalyva, M.; Papagelis, K.; Parthenios, J.; Tasis, D.; Siokou, A.; Kallitsis, I.; Galiotis, C. Carbon 2008, 46, 833-840 10.1016/j.carbon.2008.02.012
70. He, W.; Jiang, C.; Wang, J.; Lu, L. Angew. Chem., Int. Ed. 2014, 53, 9503-9507 10.1002/anie.201404333
71. Thomas, A.; Fischer, A.; Goettmann, F.; Antonietti, M.; Müller, J.-O.; Schlögl, R.; Carlsson, J. M. J. Mater. Chem. 2008, 18, 4893-4908 10.1039/b800274f
72. Zhu, J.; Faria, J. L.; Figueiredo, J. L.; Thomas, A. Chem.-Eur. J. 2011, 17, 7112-7117 10.1002/chem.201003025
73. Qiu, X.; Len, C.; Luque, R.; Li, Y. ChemSusChem 2014, 7, 1684-1688 10.1002/cssc.201301340
74. Zhang, Z.; Wang, F.; Wang, M.; Xu, S.; Chen, H.; Zhang, C.; Xu, J. Green Chem. 2014, 16, 2523-2527 10.1039/c3gc42312c
75. Isaacs, N. S. Physical organic chemistry, 2 nd ed.; Prentice Hall: Upper Saddle River, NJ, 1995; p 146.