Site-directed anchoring of an N-heterocyclic carbene on a dimetal platform: Evaluation of a pair of diruthenium(i) catalysts for carbene-transfer reactions from ethyl diazoacetate

Organometallics

Volumn 30, Issue 7, 2011, Pages 2051-2058

  Saha, Biswajit ^a   Ghatak, Tapas ^a   Sinha, Arup ^a   Rahaman, S M Wahidur ^a   Bera, Jitendra K ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE OLEFINATION; CARBENE TRANSFER; CARBENES; CHELATE BINDING; CYCLOPROPANATION; DFT CALCULATION; DIRUTHENIUM; EQUATORIAL SITES; ETHYL DIAZOACETATE; FUNCTIONALIZED; IMIDAZOL; IMIDAZOLIUM; N-HETEROCYCLIC CARBENES; NAPHTHYRIDINE; NHC LIGANDS; ROOM TEMPERATURE; SUPERIOR CATALYSTS; TETRAKIS; TRIFLUOROMETHYL;

ACETONITRILE; ALDEHYDES; BINS; BROMINE COMPOUNDS; CARBON INORGANIC COMPOUNDS; CATALYSTS; CHELATION; ELECTRONIC STRUCTURE; RUTHENIUM; RUTHENIUM COMPOUNDS;

BINDING SITES;

EID: 79953719713     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om200142p     Document Type: Article

References (70)

1. Multimetallic Catalysis in Organic Synthesis; Shibasaki, M.; Yamamoto, Y., Eds.; Wiley-VCH: Weinheim, 2004.
2. Adams, R. A.; Cotton, F. A. Catalysis by Di- and Polynuclear Metal Cluster Complexes; Wiley-VCH: New York, 1998.
3. Gambarotta, S.; Scott, J. Angew. Chem., Int. Ed. 2004, 43, 5298
4. Sinfelt, H. J. Acc. Chem. Res. 1977, 10, 15
5. Adams, R. D.; Captain, B. Angew. Chem., Int. Ed. 2008, 47, 252
6. Broussard, M. E.; Juma, B.; Train, S. G.; Peng, W.-J.; Laneman, S. A.; Stanley, G. G. Science 1993, 260, 1784
7. Nolan, S. P. N-Heterocyclic Carbenes in Synthesis; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2006; and references therein.
8. N-Heterocyclic Carbenes in Transition Metal Catalysis; Glorius, F., Ed.; Topics in Organometallic Chemistry, 21; Springer: Berlin, 2007.
9. Crabtree, R. H. J. Organomet. Chem. 2005, 690, 5451
10. Hahn, F. E.; Jahnke, M. C. Angew. Chem., Int. Ed. 2008, 47, 3122
11. Boyd, P. D. W.; Edwards, A. J.; Gardiner, M. G.; Ho, C. C.; Lemée-Cailleau, M.-H.; McGuinness, D. S.; Riapanitra, A.; Steed, J. W.; Stringer, D. N.; Yates, B. F. Angew. Chem., Int. Ed. 2010, 49, 6315
12. Diebolt, O.; Braunstein, P.; Nolan, S. P.; Cazin, C. S. J. Chem. Commun. 2008, 3190
13. Poyatos, M.; Mata, J. A.; Peris, E. Chem. Rev. 2009, 109, 3677
14. Snyder, J. P.; Padwa, A.; Stengel, T.; Arduengo, A. J., III; Jockisch, A.; Kim, H.-J. J. Am. Chem. Soc. 2001, 123, 11318
15. Gois, P. M. P.; Trindade, A. F.; Veiros, L. F.; André, V.; Duarte, M. T.; Afonso, C. A. M.; Caddick, S.; Cloke, F. G. N. Angew. Chem., Int. Ed. 2007, 46, 5750
16. Na, S. J.; Lee, B. Y.; Bui, N.-N.; Mho, S.-i.; Jang, H.-Y. J. Organomet. Chem. 2007, 692, 5523
17. Trindade, A. F.; Gois, P. M. P.; Veiros, L. F.; André, V.; Duarte, M. T.; Afonso, C. A. M.; Caddick, S.; Cloke, F. G. N. J. Org. Chem. 2008, 73, 4076
18. Gibson, S. E.; Johnstone, C.; Loch, J. A.; Steed, J. W.; Stevenazzi, A. Organometallics 2003, 22, 5374
19. van Rensburg, H.; Tooze, R. P.; Foster, D. F.; Slawin, A. M. Z. Inorg. Chem. 2004, 43, 2468
20. Poyatos, M.; McNamara, W.; Incarvito, C.; Peris, E.; Crabtree, R. H. Chem. Commun. 2007, 2267
21. Kreisel, K. A.; Yap, G. P. A.; Theopold, K. H. Chem. Commun. 2007, 1510
22. Organometallics 2006, 25, 4670.
23. Zhang, X.; Xi, Z.; Liu, A.; Chen, W. Organometallics 2008, 27, 4401
24. Ye, J.; Jin, S.; Chen, W.; Qiu, H. Inorg. Chem. Commun. 2008, 11, 404
25. Zhang, X.; Xia, Q.; Chen, W. Dalton Trans. 2009, 7045
26. Sinha, A.; Rahaman, S. M. W.; Sarkar, M.; Saha, B.; Daw, P.; Bera, J. K. Inorg. Chem. 2009, 48, 11114
27. Chang, Y.-H.; Liu, Z.-Y.; Liu, Y.-H.; Peng, S.-M.; Chen, J.-T.; Liu, S.-T. Dalton Trans. 2011, 40, 489
28. Chardon-Noblat, S.; Cripps, G. H.; Deronzier, A.; Field, J. S.; Gouws, S.; Haines, R. J.; Southway, F. Organometallics 2001, 20, 1668
29. Homanen, P.; Haukka, M.; Ahlgrén, M.; Pakkanen, T. A.; Baxter, P. N.W.; Benfield, R. E.; Connor, J. A. J. Organomet. Chem. 1998, 552, 205
30. Haukka, M.; Kiviaho, J.; Ahlgrén, M.; Pakkanen, T. A. Organometallics 1995, 14, 825
31. Bera, J. K.; Sadhukhan, N.; Majumdar, M. Eur. J. Inorg. Chem. 2009, 4023, and references therein.
32. Patra, S. K.; Majumdar, M.; Bera, J. K. J. Organomet. Chem. 2006, 691, 4779
33. Li, C.; Widjaja, E.; Garland, M. J. Am. Chem. Soc. 2003, 125, 5540
34. Li, C.; Chen, Li; Garland, M. J. Am. Chem. Soc. 2007, 129, 13327
35. Roberts, J.; Lee, C. Org. Lett. 2005, 7, 2679
36. Duschek, A.; Kirsch, S. F. Angew. Chem., Int. Ed. 2008, 47, 5703
37. Jautze, S.; Peters, R. Angew. Chem., Int. Ed. 2008, 47, 9284
38. Handa, S.; Nagawa, K.; Sohtome, Y.; Matsunaga, S.; Shibasaki, M. Angew. Chem., Int. Ed. 2008, 47, 3230
39. Yoshikai, N.; Matsuda, H.; Nakamura, E. J. Am. Chem. Soc. 2009, 131, 9590
40. Das, R. K.; Saha, B.; Rahaman, S. M. W.; Bera, J. K. Chem.Eur. J. 2010, 16, 14459
41. Doyle, M. P. Homogenous Transition Metal Catalysts in Organic Synthesis; Moser, W. R.; Slocum, D. W., Eds.; ACS Advanced Chemistry Series No. 230; American Chemical Society: Washington, DC, 1992.
42. Taber, D. F. Comprehensive Organic Synthesis; Pattenden, G., Ed.; Pergamon Press: Oxford, UK, 1991; Vol. 3, p 1045.
43. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; John Wiley and Sons: New York, 1998.
44. Doyle, M. P. Chem. Rev. 1986, 86, 919
45. Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091
46. Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797
47. Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911
48. Fructos, M. R.; Belderrain, T. R.; Nicasio, M. C.; Nolan, S. P.; Kaur, H.; Dìaz-Requejo, M. M.; Perez, P. J. J. Am. Chem. Soc. 2004, 126, 10846
49. Fructos, M. R.; Belderrain, T. R.; Frémont, P. d.; Scott, N. M.; Nolan, S. P.; Díaz-Requejo, M. M.; Pérez, P. J. Angew. Chem., Int. Ed. 2005, 44, 5284
50. Díaz-Requejo, M. M.; Pérez, P. J. Chem. Rev. 2008, 108, 3379
51. Maas, G. Chem. Soc. Rev. 2004, 33, 183
52. Maas, G.; Werle, T; Alt, M.; Mayer, D. Tetrahedron 1993, 49, 881
53. Sevryugina, Y.; Weaver, B.; Hansen, J.; Thompson, J.; Davies, H. M. L.; Petrukhina, M. A. Organometallics 2008, 27, 1750
54. 3, and EDA in 1:1.2:1 ratio. Signals corresponding to cisoid and transoid isomers were found at I 22.9 and 21.2 ppm, respectively.
55. An identical mechanism has been described for Fe(II)-porphyrin catalyst. See: Mirafzal, G. A.; Cheng, G.; Woo, L. K. J. Am. Chem. Soc. 2002, 124, 176
56. Patra, S. K.; Bera, J. K. Organometallics 2006, 25, 6054
57. Petrukhina, A.; Sevryugina, Y.; Andreini, K. W. J. Cluster Sci. 2004, 15, 451
58. SAINT+ software for CCD diffractometers; Bruker AXS: Madison, WI, 2000.
59. Sheldrick, G. M. SADABS Program for Correction of Area Detector Data; University of Göttingen: Göttingen (Germany), 1999.
60. SHELXTL Package v. 6.10; Bruker AXS: Madison, WI, 2000. Sheldrick, G. M. SHELXS-86 and SHELXL-97; University of Göttingen: Göttingen (Germany), 1997.
61. Spek, A. L. PLATON; University of Utrecht (The Netherlands), 2001.
62. Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565
63. Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules; Oxford University Press: Oxford, U.K., 1989.
64. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
65. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1998, 37, 785
66. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270
67. Wadt, W. R.; Hay, P. J. J. Chem. Phys. 1985, 82, 284
68. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299
69. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; 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.; Pople, J. A. Gaussian 03; Gaussian, Inc.: Pittsburgh, PA, 2003.
70. Reed, A. E.; Weinstock, R. B.; Weinhold, F. J. Chem. Phys. 1985, 83, 735