Hydrogen-Free Cobalt-Rhodium Heterobimetallic Nanoparticle-Catalyzed Reductive Amination of Aldehydes and Ketones with Amines and Nitroarenes in the Presence of Carbon Monoxide and Water

ACS Catalysis

Volumn 5, Issue 8, 2015, Pages 4846-4850

  Park, Jang Won ^a   Chung, Young Keun ^a  

^a Seoul National University   (South Korea)

Author keywords

amination; carbon monoxide; heterogeneous catalysis; reduction; water

Indexed keywords

ALDEHYDES; AMINATION; CARBON MONOXIDE; CATALYSIS; CATALYST ACTIVITY; CHEMICAL SHIFT; COBALT; KETONES; METALLIC COMPOUNDS; NANOPARTICLES; REDUCTION; RHODIUM; WATER; WATER GAS SHIFT;

CATALYTIC SYSTEM; CHEMICAL EQUATIONS; HETEROBIMETALLICS; HYDROGEN SOURCES; NITROARENES; REACTION CONDITIONS; REDUCTIVE AMINATION; WATER GAS SHIFT (WGS) REACTION;

AMINES;

EID: 84938702295     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/acscatal.5b01198     Document Type: Article

References (45)

1. Xu, Z.; Yan, P.; Xu, W.; Jia, S.; Xia, Z.; Chung, B.; Zhang, Z. C. RSC Adv. 2014, 4, 59083-59087 10.1039/C4RA10349A
2. Zhu, M. Catal. Lett. 2014, 144, 1568-1572 10.1007/s10562-014-1314-5
3. Zhou, S.; Fleischer, S.; Jiao, H.; Junge, K.; Beller, M. Adv. Synth. Catal. 2014, 356, 3451-3455 10.1002/adsc.201400328
4. Storer, R. I.; Carrera, D. E.; Ni, Y.; Macmillan, D. W. C. J. Am. Chem. Soc. 2006, 128, 84-86 10.1021/ja057222n
5. Zhou, J.; List, B. J. Am. Chem. Soc. 2007, 129, 7498-7499 10.1021/ja072134j
6. Koszelewski, D.; Lavandera, I.; Clay, D.; Guebitz, G. M.; Rozzell, D.; Kroutil, W. Angew. Chem., Int. Ed. 2008, 47, 9337-9340 10.1002/anie.200803763
7. Williams, G. D.; Pike, R. A.; Wade, C. E.; Wills, M. Org. Lett. 2003, 5, 4227-4230 10.1021/ol035746r
8. Kadyrov, R.; Riermeier, T. H. Angew. Chem., Int. Ed. 2003, 42, 5472-5474 10.1002/anie.200352503
9. Chi, Y.; Zhou, Y. G.; Zhang, X. J. Org. Chem. 2003, 68, 4120-4122 10.1021/jo026856z
10. Kadyrov, R.; Riermeier, T. H.; Dingerdissen, U.; Tararov, V.; Börner, A. J. Org. Chem. 2003, 68, 4067-4070 10.1021/jo020690k
11. Chang, M.; Liu, S.; Huang, K.; Zhang, X. Org. Lett. 2013, 15, 4354-4357 10.1021/ol401851c
12. Pagnoux-Ozherelyeva, A.; Pannetier, N.; Mbaye, M. D.; Gaillard, S.; Renaud, J.-L. Angew. Chem., Int. Ed. 2012, 51, 4976 10.1002/anie.201201360
13. Nasrollahzadeh, M. New J. Chem. 2014, 38, 5544-5550 10.1039/C4NJ01440E
14. Borch, R. F.; Bernstein, M. D.; Durst, H. D. J. Am. Chem. Soc. 1971, 93, 2897-2904 10.1021/ja00741a013
15. Sato, S.; Sakamoto, T.; Miyazawa, E.; Kikugawa, Y. Tetrahedron 2004, 60, 7899-7906 10.1016/j.tet.2004.06.045
16. Kadyrov, R.; Riermeier, T. H. Angew. Chem., Int. Ed. 2003, 42, 5472-5474 10.1002/anie.200352503
17. Wang, C.; Pettman, A.; Basca, J.; Xiao, J. Angew. Chem., Int. Ed. 2010, 49, 7548-7552 10.1002/anie.201002944
18. Wei, Y.; Wang, C.; Jiang, X.; Xue, D.; Li, J.; Xiao, J. Chem. Commun. 2013, 49, 5408-5410 10.1039/c3cc41661e
19. Talwar, D.; Salguero, N. P.; Robertson, C. M.; Xiao, J. Chem. - Eur. J. 2014, 20, 245-252 10.1002/chem.201303541
20. Chusov, D.; List, B. Angew. Chem., Int. Ed. 2014, 53, 5199-5201 10.1002/anie.201400059
21. Iqbal, A. F. M. Tetrahedron Lett. 1971, 12 (37) 3385-3388 10.1016/S0040-4039(01)97185-0
22. Astruc, D.; Lu, F.; Aranzaes, J. R. Angew. Chem., Int. Ed. 2005, 44, 7852-7872 10.1002/anie.200500766
23. Yan, N.; Xiao, C.; Kou, Y. Coord. Chem. Rev. 2010, 254, 1179-1218 10.1016/j.ccr.2010.02.015
24. Shylesh, S.; Schunemann, V.; Thiel, W. R. Angew. Chem., Int. Ed. 2010, 49, 3428-3459 10.1002/anie.200905684
25. Polshettiwar, V.; Luque, R.; Fihri, A.; Zhu, H.; Bouhrara, M.; Basset, J.-M. Chem. Rev. 2011, 111, 3036-3075 10.1021/cr100230z
26. Park, K. H.; Son, S. U.; Chung, Y. K. Chem. Commun. 2003, 1898-1899 10.1039/b304325h
27. Park, K. H.; Son, S. U.; Chung, Y. K. Org. Lett. 2002, 4, 4361-4363 10.1021/ol027089t
28. Park, J. H.; Chung, Y. K. Dalton Trans. 2008, 2369-2378 10.1039/b718609f
29. Park, J. H.; Kim, S. Y.; Kim, S. M.; Lee, S.; Chung, Y. K. Synlett 2007, 453-459 10.1055/s-2007-967986
30. Park, J. H.; Kim, E.; Chung, Y. K. Org. Lett. 2008, 10, 4719-4721 10.1021/ol801978n
31. Gülak, S.; Wu, L.; Liu, Q.; Franke, R.; Jackstell, R.; Beller, M. Angew. Chem., Int. Ed. 2014, 53, 7320-7323 10.1002/anie.201402368
32. Kolesnikov, P. N.; Yagafarov, N. Z.; Usanov, D. L.; Maleev, V. I.; Chusov, D. Org. Lett. 2015, 17, 173-175 10.1021/ol503595m
33. Knifton, J. F. J. Org. Chem. 1976, 41, 1200-1206 10.1021/jo00869a025
34. Harsy, S. G. Tetrahedron 1990, 46, 7403-7412 10.1016/S0040-4020(01)89056-6
35. Blaser, H. U.; Steiner, H.; Studer, M. ChemCatChem 2009, 1, 210-221 10.1002/cctc.200900129
36. Kim, J. H.; Park, J. H.; Chung, Y. K.; Park, K. H. Adv. Synth. Catal. 2012, 354, 2412-2418 10.1002/adsc.201200356
37. Cann, K.; Cole, T.; Slegeir, W.; Pettit, R. J. Am. Chem. Soc. 1978, 100, 3969-3971 10.1021/ja00480a075
38. Kaneda, K.; Hiraki, M.; Imanaka, T.; Teranishi, S. J. Mol. Catal. 1981, 12, 385-387 10.1016/0304-5102(81)85043-2
39. Watanabe, Y.; Tsuji, Y.; Ohsumi, T.; Takeuchi, R. Tetrahedron Lett. 1983, 24, 4121-4122 10.1016/S0040-4039(00)88277-5
40. Shvo, Y.; Czarkie, D. J. Organomet. Chem. 1989, 368, 357-365 10.1016/0022-328X(89)85414-2
41. Liu, L.; Qiao, B.; Chen, Z.; Zhang, J.; Deng, Y. Chem. Commun. 2009, 653-655 10.1039/B816547E
42. Sreedhar, B.; Reddy, P. S.; Devi, D. K. J. Org. Chem. 2009, 74, 8806-8809 10.1021/jo901787t
43. Tang, C.-H.; He, L.; Liu, Y.-M.; Cao, Y.; He, H.-Y.; Fan, K.-N. Chem. - Eur. J. 2011, 17, 7172-7177 10.1002/chem.201100393
44. Li, L.; Niu, Z.; Cai, S.; Zhi, Y.; Li, H.; Rong, H.; Liu, L.; Liu, L.; He, W.; Li, Y. Chem. Commun. 2013, 49, 6843-6845 10.1039/c3cc00249g
45. Stemmler, T.; Westerhaus, F. A.; Surkus, A.-E.; Pohl, M.-M.; Junge, K.; Beller, M. Green Chem. 2014, 16, 4535-4540 10.1039/C4GC00536H