Chemoselective Hydrogenation and Transfer Hydrogenation of Olefins and Carbonyls with the Cluster-Derived Ruthenium Nanocatalyst in Water

ChemCatChem

Volumn 5, Issue 1, 2013, Pages 322-330

  Indra, Arindam ^a   Maity, Prasenjit ^a   Bhaduri, Sumit ^a   Lahiri, Goutam Kumar ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

Chemoselectivity; Hydrogenation; Nanocatalyst; Ruthenium; Transfer hydrogenation; Water soluble polymer

Indexed keywords

ACETOPHENONES; AROMATIC RINGS; CATALYTIC SYSTEM; CHEMO-SELECTIVITY; CHEMOSELECTIVE HYDROGENATION; CRYSTAL PLANES; CYCLOHEXANONES; HIGH-RESOLUTION TEM; HYDROGEN DONOR; HYDROGENATION REACTIONS; ION PAIRING; METHYL PYRUVATE; NANO-CATALYST; POLY (DIALLYLDIMETHYLAMMONIUM CHLORIDE); QUATERNARY AMMONIUM GROUP; RUTHENIUM NANOPARTICLES; SAFFLOWER OIL; TRANSFER HYDROGENATIONS; TURNOVER NUMBER; WATERSOLUBLE POLYMERS;

ALDEHYDES; CATALYSTS; CHLORINE COMPOUNDS; HYDROGEN; KETONES; METHANOL; OLEFINS; ORGANIC COMPOUNDS; RUTHENIUM; RUTHENIUM COMPOUNDS; VEGETABLE OILS;

HYDROGENATION;

EID: 84871652413     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201200448     Document Type: Article

References (71)

1. M. O. Simon, C. J. Li, Chem. Soc. Rev. 2012, 41, 1415-1427.
2. H. Syska, W. A. Herrmann, F. E. Kuehn, J. Organomet. Chem. 2012, 703, 56-62;
3. D. B. Bagal, Z. S. Qureshi, K. P. Dhake, S. R. Khan, B. M. Bhanage, Green Chem. 2011, 13, 1490-1494;
4. G. Liu, H. Gu, Y. Sun, J. Long, Y. Xu, H. Li, Adv. Synth. Catal. 2011, 353, 1317-1324;
5. Y. Q. Sun, G. H. Liu, H. Y. Gu, T. Z. Huang, Y. L. Zhang, H. X. Li, Chem. Commun. 2011, 47, 2583-2585;
6. I. Nieto, M. S. Livings, J. B. Sacci, L. E. Reuther, M. Zeller, E. T. Papish, Organometallics 2011, 30, 6339-6342;
7. K. H. Shaughnessy, Chem. Rev. 2009, 109, 643-710;
8. C. J. Li, Chem. Rev. 2005, 105, 3095-3165;
9. R. A. Sheldon, Green Chem. 2005, 7, 267-278;
10. H. U. Blaser, M. Studer, Green Chem. 2003, 5, 112-117;
11. U. M. Lindström, Chem. Rev. 2002, 102, 2751-2772;
12. F. Joo, Aqueous Organometallic Catalysis, Vol.23, Kluwer Academic Pub., Dordrecht, 2001;
13. Organic Synthesis in Water (Ed.: P.A. Grieco), Blackie, London, 1998;
14. Aqueous-phase Organometallic Catalysis: Concepts and Applications (Eds.: B. Cornils, W.A. Herrmann), Wiley-VCH, Weinheim, 1998.
15. D. S. Wang, Q. A. Chen, S. M. Lu, Y. G. Zhou, Chem. Rev. 2012, 112, 2557-2590;
16. M. J. Beier, J. M. Andanson, T. Mallat, F. Krumeich, A. Baiker, ACS Catal. 2012, 2, 337-340;
17. J. H. Xie, S. F. Zhu, Q. L. Zhou, Chem. Rev. 2011, 111, 1713-1760;
18. P. D. Burton, T. J. Boyle, A. K. Datye, J. Catal. 2011, 280, 145-154;
19. N. Yan, C. Zhao, C. Luo, P. J. Dyson, H. Liu, Y. Kou, J. Am. Chem. Soc. 2006, 128, 8714-8715.
20. A. Robertson, T. Matsumoto, S. Ogo, Dalton Trans. 2011, 40, 10304-10310.
21. J. F. B. Hall, X. Han, M. Poliakoff, R. A. Bourne, M. W. George, Chem. Commun. 2012, 48, 3073-3075;
22. P. J. Debouttière, Y. Coppel, A. D. Nowicki, A. Roucoux, B. Chaudret, K. Philippot, Eur. J. Inorg. Chem. 2012, 1229-1236;
23. Y. Lan, M. Zhang, W. Zhang, L. Yang, Chem. Eur. J. 2009, 15, 3670-3673;
24. A. Behr, M. Urschey, V. A. Brehme, Green Chem. 2003, 5, 198-204.
25. X. P. Fu, L. Liu, D. Wang, Y. J. Chen, C. J. Li, Green Chem. 2011, 13, 549-553;
26. V. V. Fokin, K. B. Sharpless, Angew. Chem. 2001, 113, 3563-3565; Angew. Chem. Int. Ed. 2001, 40, 3455-3457;
27. N. Jiang, A. J. Ragauskas, Tetrahedron Lett. 2006, 47, 197-200;
28. J. C. Morita, H. Nakatsuji, T. Misaki, Y. Tanabe, Green Chem. 2005, 7, 711-715;
29. J. Mao, B. Wan, F. Wu, S. Lu, Tetrahedron Lett. 2005, 46, 7341-7344;
30. X. Xu, T. Hirao, J. Org. Chem. 2005, 70, 8594-8596;
31. S. Narayan, J. Muldoon, M. G. Finn, V. V. Fokin, H. C. Kolb, K. B. Sharpless, Angew. Chem. 2005, 117, 3339-3343; Angew. Chem. Int. Ed. 2005, 44, 3275-3279;
32. J. E. Klijn, J. B. F. N. Engberts, Nature 2005, 435, 746-747;
33. M. D. Hughes, Y.-J. Xu, P. Jenkins, P. Mcmorn, P. London, D. I. Enache, A. F. Carley, G. A. Attard, G. J. Hutchings, F. King, E. H. Stitt, P. Johnston, K. Griffin, C. J. Kiely, Nature 2005, 437, 1132-1135.
34. N. Yan, C. Xiao, Y. Kou, Coord. Chem. Rev. 2010, 254, 1179-1218.
35. A. Indra, M. Doble, S. Bhaduri, G. K. Lahiri, ACS Catal. 2011, 1, 511-518.
36. A. Indra, S. Basu, D. G. Kulkarni, C. S. Gopinath, S. Bhaduri, G. K. Lahiri, Appl. Catal. A 2008, 344, 124-130.
37. S. Basu, M. Mapa, C. S. Gopinath, M. Doble, S. Bhaduri, G. K. Lahiri, J. Catal. 2006, 239, 154-161.
38. S. Basu, H. Paul, C. S. Gopinath, S. Bhaduri, G. K. Lahiri, J. Catal. 2005, 229, 298-302.
39. S. Bhaduri, G. K. Lahiri, P. Munshi, D. Mukesh, Catal. Lett. 2000, 65, 61-65.
40. S. Bhaduri, V. S. Darshane, K. Sharma, D. Mukesh, Chem. Commun. 1992, 1738-1740.
41. S. Bhaduri, K. R. Sharma, Dalton Trans. 1984, 2309-2313.
42. A. Indra, N. Maity, P. Maity, S. Bhaduri, G. K. Lahiri, J. Catal. 2011, 284, 176-183.
43. P. Maity, C. S. Gopinath, S. Bhaduri, G. K. Lahiri, Green Chem. 2009, 11, 554-561.
44. P. Maity, S. Basu, S. Bhaduri, G. K. Lahiri, Adv. Synth. Catal. 2007, 349, 1955-1962.
45. P. Maity, S. Basu, S. Bhaduri, G. K. Lahiri, J. Mol. Catal. A-Chem. 2007, 270, 117-122.
46. J. Wang, H. F. M. Boelens, M. B. Thathagar, G. Rothenberg, ChemPhysChem 2004, 5, 93-98;
47. X. Yan, H. Liu, K. Y. Liew, J. Mater. Chem. 2001, 11, 3387-3391.
48. M. Y. Jung, Y. L. Ha, J. Agric. Food Chem. 1999, 47, 704-708;
49. B. L. A. PrabhavathiDevi, M. S. L. Karuna, K. N. Rao, P. S. Saiprasad, R. B. N. Prasad, J. Am. Oil Chem. Soc. 2003, 80, 1003-1005.
50. R. N. Butler, A. G. Coyne, Chem. Rev. 2010, 110, 6302-6337.
51. R. Breslow, Acc. Chem. Res. 1991, 24, 159-164.
52. Y. S. Jung, R. A. Marcus, J. Am. Chem. Soc. 2007, 129, 5492-5502.
53. S. Bhaduri, K. Sharma, D. Mukesh, J. Chem. Soc. Dalton Trans. 1993, 1191-1199.
54. J. Dimroth, U. Schedler, J. Keilitz, R. Haag, R. Schomckera, Adv. Synth. Catal. 2011, 353, 1335-1344;
55. Z. Weng, S. Muratsugu, N. Ishiguro, S. Ohkoshi, M. Tada, Dalton Trans. 2011, 40, 2338-2347.
56. M. Zahmakiran, Y. Tonbul, S. Özkar, J. Am. Chem. Soc. 2010, 132, 6541-6549.
57. M. Zahmakiran, Y. Tonbul, S. Özkar, Appl. Catal. B-Environ. 2010, 96, 533-540.
58. M. Takasaki, Y. Motoyama, K. Higashi, S. H. Yoon, I. Mochida, H. Nagashima, Chem. Asian J. 2007, 2, 1524-1533;
59. M. Takasaki, Y. Motoyama, S. H. Yoon, I. Mochida, H. Nagashima, J. Org. Chem. 2007, 72, 10291-10293.
60. G. Süss-Fink, M. Faure, T. R. Ward, Angew. Chem. 2002, 114, 105-108; Angew. Chem. Int. Ed. 2002, 41, 99-101.
61. C. M. Hagen, L. Vieille-Petit, G. Laurenczy, G. Süss-Fink, R. G. Finke, Organometallics 2005, 24, 1819-1831.
62. J. A. Widegren, M. A. Bennett, R. G. Finke, J. Am. Chem. Soc. 2003, 125, 10301-10310.
63. R. Raja, T. Khimyak, J. M. Thomas, S. Hermans, B. F. G. Johnson, Angew. Chem. 2001, 113, 4774-4778; Angew. Chem. Int. Ed. 2001, 40, 4638-4642.
64. C. A. Jaska, I. J. Manners, J. Am. Chem. Soc. 2004, 126, 9776-9785;
65. R. Rousseau, G. K. Schenter, J. L. Fulton, J. C. Linehan, M. H. Engelhard, T. Autrey, J. Am. Chem. Soc. 2009, 131, 10516-10524.
66. E. Bayram, J. C. Linehan, J. L. Fulton, J. A. S. Roberts, N. K. Szymczak, T. D. Smurthwaite, S. Özkar, M. Balasubramanian, R. G. Finke, J. Am. Chem. Soc. 2011, 133, 18889-18902.
67. E. Schmidt, A. Vargas, T. Mallat, A. Baiker, J. Am. Chem. Soc. 2009, 131, 12358-12367.
68. C. A. Witham, W. Huang, C. K. Tsung, J. N. Kuhn, G. A. Somorjai, F. D. Toste, Nat. Chem. 2010, 2, 36-41.
69. D. Y. Murzin, J. Catal. 2010, 276, 85-91.
70. J. W. Koepke, J. R. Johnson, S. A. R. Knox, H. D. Kaesz, J. Am. Chem. Soc. 1975, 97, 3947-3972.
71. thed., Blackwell Scientific Publications Ltd., Oxford, 1987, pp.88.