Isomeric complexes of [RuII(trpy)(L)Cl] (trpy = 2,2′:6′,2″-terpyridine and HL = quinaldic acid): Preference of isomeric structural form in catalytic chemoselective epoxidation process

Inorganic Chemistry

Volumn 50, Issue 5, 2011, Pages 1775-1785

  Chowdhury, Abhishek Dutta ^a   Das, Amit ^a   Irshad, K ^a   Mobin, Shaikh M ^a   Lahiri, Goutam Kumar ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY BOMBAY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84962433665     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic102195w     Document Type: Article

References (104)

1. Barf, G. A. and Sheldon, R. A. J. Mol. Catal. A: Chem. 1995, 102, 23 and references cited therein
2. Sheldon, R. A. and Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981.
3. Bäckvall, J.-E. Modern Oxidation Methods; Wiley-VCH: Weinheim, Germany, 2004.
4. Sheldon, R. A., Arends, I., and Hanefeld, U. Green Chemistry and Catalysis; Wiley-VCH: Weinheim, Germany, 2007.
5. Weissermel, K. and Arpe, H.-J. Industrial Organic Chemistry, 4 th ed.; Wiley-VCH: Weinheim, Germany, 2003.
6. Crawford, K., Rautenstrauch, V., and Uijttewaal, A. Synlett 2001, 1127
7. Wahren, U., Sprung, I., Schulze, K., Findeisen, M., and Buchbauer, G. Tetrahedron Lett. 1999, 40, 5991
8. Kelly, D. R. and Nally, J. Tetrahedron Lett. 1999, 40, 3251
9. Grigoropoulou, G., Clark, J. H., and Elings, J. A. Green Chem. 2003, 5, 1
10. Lane, B. S. and Burgess, K. Chem. Rev. 2003, 103, 2457
11. Beller, M. Adv. Synth. Catal. 2004, 346, 107
12. Legros, J. and Bolm, C. Chem.-Eur. J. 2005, 11, 1086
13. Bregeault, J. M. Dalton Trans. 2003, 3289
14. Herrmann, W. A., Fischer, R. W., and Marz, D. W. Angew. Chem., Int. Ed. 1991, 30, 1638
15. Rudolf, J., Reddy, K. L., Chiang, J. P., and Sharpless, K. B. J. Am. Chem. Soc. 1997, 119, 6189
16. Hermann, W. A., Kratzer, R. M., Ding, H., Thiel, W. R., and Glas, H. J. Organomet. Chem. 1998, 555, 293
17. Shi, Y. Acc. Chem. Res. 2004, 37, 488
18. Gerlach, A. and Geller, T. Adv. Synth. Catal. 2004, 346, 1247
19. Yang, D. Acc. Chem. Res. 2004, 37, 497
20. Johnson, R. A. and Sharpless, K. B. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.1.
21. Katsuki, T. and Martin, V. S. Org. React. 1996, 48, 1
22. Jacobsen, E. N. Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; Chapter 4.2.
23. Katsuki, T. Adv. Synth. Catal. 2002, 344, 131
24. Cavallo, L. and Jacobsen, H. Angew. Chem., Int. Ed. 2000, 39, 589
25. Nishiyama, H., Shimada, T., Itoh, H., Sugiyama, H., and Motoyama, Y. Chem. Commun. 1997, 1863
26. End, N. and Pfaltz, A. Chem. Commun. 1998, 589
27. Gross, Z. and Ini, S. Org. Lett. 1999, 1, 2077 and references therein
28. Stoop, R. M., Bachmann, S., Valentini, M., and Mezzetti, A. Organometallics 2000, 19, 4117
29. Pezet, F., Aït-Haddou, H., Daran, J.-C., Sadaki, I., and Balavoine, G. G. A. Chem. Commun. 2002, 510
30. Takeda, T., Irie, R., Shinoda, Y., and Katsuki, T. Synlett 1999, 1157
31. Nakata, K., Takeda, T., Mihara, J., Hamada, T., Irie, R., and Katsuki, T. Chem.-Eur. J. 2001, 7, 3776
32. Dakkach, M., Isabel López, M., Romero, I., Rodríguez, M., Atlamsani, A., Parella, T., Fontrodona, X., and Llobet, A. Inorg. Chem. 2010, 49, 5977
33. Chatterjee, D. Inorg. Chim. Acta 2008, 361, 2177
34. Chatterjee, D., Sengupta, A., and Mitra, A. Polyhedron 2007, 26, 178
35. Benet-Buchholz, J., Comba, P., Llobet, A., Roeser, S., Vadivelu, P., Wadepohl, H., and Wiesner, S. Dalton Trans. 2009, 5910
36. Klawonn, M., Tse, M. K., Bhor, S., Döbler, C., and Beller, M. J. Mol. Catal. A 2004, 218, 13
37. Tse, M. K., Bhor, S., Klawonn, M., Döbler, C., and Beller, M. Tetrahedron Lett. 2003, 44, 7479
38. Bhor, S., Tse, M. K., Klawonn, M., Döbler, C., Beller, M., and Mägerlein, W. Adv. Synth. Catal. 2004, 346, 263
39. Tse, M. K., Döbler, C., Bhor, S., Klawonn, M., Mägerlein, W., Hugl, H., and Beller, M. Angew. Chem., Int. Ed. 2004, 43, 5255
40. Tse, M. K., Bhor, S., Klawonn, M., Anilkumar, G., Jiao, H., Spannenberg, S., Döbler, C., Mägerlein, W., Hugl, H., and Beller, M. Chem.-Eur. J. 2006, 12, 1875
41. Tse, M. K., Bhor, S., Klawonn, M., Bhor, S., Döbler, C., Anilkumar, G., Hugl, H., Mägerlein, W., and Beller, M. Org. Lett. 2005, 7, 987
42. Schröder, K., Enthaler, S., Join, B., Junge, K., and Beller, M. Adv. Synth. Catal. 2010, 352, 1771
43. Kundu, T., Sarkar, B., Mondal, T. K., Fiedler, J., Mobin, S. M., Kaim, W., and Lahiri, G. K. Inorg. Chem. 2010, 49, 6565
44. Patra, S., Sarkar, B., Ghumaan, S., Patil, M. P., Mobin, S. M., Sunoj, R. B., Kaim, W., and Lahiri, G. K. Dalton Trans. 2005, 1188
45. Sarkar, S., Sarkar, B., Chanda, N., Kar, S., Mobin, S. M., Fiedler, J., Kaim, W., and Lahiri, G. K. Inorg. Chem. 2005, 44, 6092
46. Chanda, N., Paul, D., Kar, S., Mobin, S. M., Datta, A., Puranik, V. G., Rao, K. K., and Lahiri, G. K. Inorg. Chem. 2005, 44, 3499
47. Chanda, N., Mobin, S. M., Puranik, V. G., Dutta, A., Niemeyer, M., and Lahiri, G. K. Inorg. Chem. 2004, 43, 1056
48. Mondal, B., Puranik, V. G., and Lahiri, G. K. Inorg. Chem. 2002, 41, 5831
49. De, P., Sarkar, B., Maji, S., Das, A. K., Bulak, E., Mobin, S. M., Kaim, W., and Lahiri, G. K. Eur. J. Inorg. Chem. 2009, 2702
50. Das, A. K., Sarkar, B., Duboc, C., Strobel, S., Fiedler, J., Zalis, S., Lahiri, G. K., and Kaim, W. Angew. Chem., Int. Ed. 2009, 48, 4242
51. Sans, C., Rodriguez, M., Romero, I., and Llobet, A. Inorg. Chem. 2003, 42, 8385
52. Hartshorn, C. M., Maxwell, K. A., White, P. S., DeSimone, J. M., and Meyer, T. J. Inorg. Chem. 2001, 40, 601
53. Zhang, H.-J., Demerseman, B., Toupet, L., Xi, Z., and Bruneau, C. Organometallics 2009, 28, 5173
54. Llobet, A., Doppelt, P., and Meyer, T. J. Inorg. Chem. 1988, 27, 514
55. Anastas, P. T. and Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: New York, 1998; p 30.
56. Capello, C., Fischer, U., and Hungerbuhler, K. Green Chem. 2007, 9, 927
57. Marky, I. E., Giles, P. R., Tsukazaki, M., Brown, S. M., and Urch, C. J. Science 1996, 274, 2044
58. Brink, G.-J., Arends, I. W. C. E., and Sheldon, R. A. Science 2000, 287, 1636
59. Nishiyama, Y., Nakagawa, Y., and Mizuno, N. Angew. Chem., Int. Ed. 2001, 40, 3639
60. Khenkin, A. M., Shimon, L. J. W., and Neumann, R. Inorg. Chem. 2003, 42, 3331
61. Döbler, C., Mehltretter, G. M., Sundermeier, U., and Beller, M. J. Organomet. Chem. 2001, 621, 70
62. Groves, J. T. and Quinn, R. J. Am. Chem. Soc. 1985, 107, 5790
63. Paeng, I. R. and Nakamoto, K. J. Am. Chem. Soc. 1990, 112, 3289
64. Strukul, G. Catalytic Oxidations with Hydrogen Peroxide as Oxidant; Kluwer Academic: Dordrecht, The Netherlands, 1992.
65. Jones, C. W. Applications of Hydrogen Peroxide and Derivatives; Royal Society of Chemistry: Cambridge, U. K., 1999.
66. Elvers, B., Hawkins, S., Ravenscroft, M., and Schulz, G. Ullmann's Encyclopedia of Industrial Chemistry, 5 th ed.; VCH: New York, 1989; Vol. A13, p 443.
67. Kroschwitz, J. I. and Howe-Grant, M. Kirk-Othmer Encyclopedia of Chemical Technology, 4 th ed.; Wiley: New York, 1995; Vol. 13, p 961.
68. Dutta, P. K. and Das, S. K. J. Am. Chem. Soc. 1997, 119, 4311
69. Taqui Khan, M. M., Chatterjee, D., Samad, S. A., and Merchant, R. R. J. Mol. Catal. 1990, 61, 55
70. Moyer, B. A., Sipe, B. K., and Meyer, T. J. Inorg. Chem. 1981, 20, 1475
71. Douglas, E., Paull, M. D., Blair, A., Keagy, M. D., Eric, J., Kron, B. S., Benson, R., and Wilcox, M. D. J. Surg. Res. 1989, 46, 333
72. Bunda, S., Kaviani, N., and Hinek, A. J. Biol. Chem. 2005, 280, 2341
73. Acquaye, J. H., Muller, J. G., and Takeuchi, K. J. Inorg. Chem. 1993, 32, 160
74. Lai, S., Lepage, C. J., and Lee, D. G. Inorg. Chem. 2002, 41, 1954
75. Hamelin, O., Ménage, S., Charnay, F., Chavarot, V, Pierre, J.-L., Pécaut, J., and Fontecave, M. Inorg. Chem. 2008, 47, 6413
76. Chavarot, M., Ménage, S., Hamelin, O., Charnay, F., Pécaut, J., and Fontecave, M. Inorg. Chem. 2003, 42, 4810
77. Groves, J. T. and Kruper, W. J. J. Am. Chem. Soc. 1979, 101, 7613
78. Groves, J. T. and Meyers, R. S. J. Am. Chem. Soc. 1983, 105, 5786
79. Jørgensen, K. A. Chem. Rev. 1989, 89, 431
80. Meunier, B. Chem. Rev. 1992, 92, 1411
81. Jørgensen, K. A. and Schiøtt, B. Chem. Rev. 1990, 90, 1483
82. Ostovic, D. and Bruice, T. C. Acc. Chem. Res. 1992, 25, 314
83. Fung, W.-H., Yu, W.-Y., and Che, C.-M. J. Org. Chem. 1998, 63, 7715
84. Sullivan, B. P., Calvert, J. M., and Meyer, T. J. Inorg. Chem. 1980, 19, 1404
85. Perrin, D. D., Armarego, W. L. F., and Perrin, D. R. Purification of Laboratory Chemicals, 2 nd ed.; Pergamon: New York, 1980.
86. Sheldrick, G. M. SHELX-97; University of Göttingen: Göttingen, Germany, 1997.
87. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
88. Lee, C., Yang, W., and Parr, R. G. Phys. Rev. B 1998, 37, 785
89. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Montgomery, J. A., Vreven, T., Jr., Kudin, K. N., Burant, J. C., Millam, J. M., Iyengar, S. S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G. A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J. E., Hratchian, H. P., Cross, J. B., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Ayala, P. Y., Morokuma, K., Voth, G. A., Salvador, P., Dannenberg, J. J., Zakrzewski, V. G., Dapprich, S., Daniels, A. D., Strain, M. C., Farkas, O., Malick, D. K., Rabuck, A. D., Raghavachari, K., Foresman, J. B., Ortiz, J. V., Cui, Q., Baboul, A. G., Clifford, S., Cioslowski, J., Stefanov, B. B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R. L., Fox, D. J., Keith, T., Al-Laham, M. A., Peng, C. Y., Nanayakkara, A., Challacombe, M., Gill, P. M. W., Johnson, B., Chen, W., Wong, M. W., Gonzalez, C., and Pople, J. A. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
90. Dunning, T. H., Jr. and Hay, P. J. In Modern Theoretical Chemistry; Schaefer, H. F., III, Ed.; Plenum: New York, 1976; p 1.
91. Hay, P. J. and Wadt, W. R. J. Chem. Phys. 1985, 82, 299
92. Bauernschmitt, R. and Ahlrichs, R. Chem. Phys. Lett. 1996, 256, 454
93. Stratmann, R. E., Scuseria, G. E., and Frisch, M. J. J. Chem. Phys. 1998, 109, 8218
94. Casida, M. E., Jamorski, C., Casida, K. C., and Salahub, D. R. J. Chem. Phys. 1998, 108, 4439
95. Miertus, S., Scrocco, E., and Tomasi, J. Chem. Phys. 1981, 55, 117
96. Cossi, M., Barone, V., Cammi, R., and Tomasi, J. Chem. Phys. Lett. 1996, 255, 327
97. Barone, V. and Cossi, M. J. Chem. Phys. A 1998, 102, 1995
98. O'Boyle, N. M. GaussSum 2.1, 2007. Available at http://gausssum.sf.net (accessed Jan 2011).
99. O'Boyle, N. M., Tenderholt, A. L., and Langner, K. M. J. Comput. Chem. 2008, 29, 839
100. Glendening, E. D., Reed, A. E., Carpenter, J. E., and Weinhold, F. NBO, version 3.1; Theoretical Chemistry Institute, University of Wisconsin: Madison, WI, 2001.
101. Reed, A. E. and Weinhold, F. J. Chem. Phys. 1985, 83, 1736
102. Reed, A. E., Curtiss, L. A., and Weinhold, F. Chem. Rev. 1988, 88, 899
103. Weinhold, F. In Encyclopedia of Computational Chemistry; Schleyer, P. v. R., Ed.; Wiley: New York, 1998; p 1792.
104. Zhurko, D. A. and Zhurko, G. A. ChemCraft 1.5; Plimus: San Diego, CA. http://www.chemcraftprog.com (accessed Jan 2011).