Synthesis and catalytic evaluation of ruthenium-arene complexes generated using imidazol(in)ium-2-carboxylates and dithiocarboxylates

Organometallics

Volumn 28, Issue 14, 2009, Pages 4056-4064

  Delaude, Lionel ^a   Sauvage, Xavier ^a   Demonceau, Albert ^a   Wouters, Johan ^b  

^a UNIVERSITY OF LIÈGE   (Belgium)

^b UNIVERSITY OF NAMUR   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ANALYTICAL TECHNIQUES; CATALYTIC APPLICATIONS; CATALYTIC EVALUATION; CATIONIC COMPLEXES; CYCLOHEXYL; HIGH YIELD; IMIDAZOL; IMIDAZOLIUM; IN-LINE; IN-SITU; NITROGEN ATOM; P-CYMENE; RING OPENING METATHESIS; RUTHENIUM-ARENE; TRANSITION-METAL COMPLEX;

ATOM TRANSFER RADICAL POLYMERIZATION; ATOMS; BEARINGS (STRUCTURAL); CARBOXYLATION; DYES; FREE RADICAL REACTIONS; METAL COMPLEXES; RUTHENIUM; SYNTHESIS (CHEMICAL); TRANSITION METALS; X RAY DIFFRACTION ANALYSIS;

RUTHENIUM COMPOUNDS;

EID: 67651030408     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9002363     Document Type: Article

References (89)

1. For monographs, see: (a) Carbene Chemistry: From Fleeting Intermediates to Powerful Reagents; Bertrand, G., Ed.; Marcel Dekker: New York, 2002.
2. (b) N-Heterocyclic Carbenes in Synthesis; Nolan, S. P., Ed.; Wiley-VCH: Weinheim, 2006.
3. (c) N-Heterocyclic Carbenes in Transition Metal Catalysis; Glorius, F., Ed.; Topics in Organometallic Chemistry, Vol. 21; Springer: Berlin, 2007.
4. For reviews, see: (a) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162-2187.
5. (b) Jafarpour, L.; Nolan, S. P. Adv. Organomet. Chem. 2001, 46, 181-222.
6. (c)Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309.
7. (d) Herrmann, W. A.; Weskamp, T.; Böhm, V. P. W. Adv. Organomet. Chem. 2002, 48, 1-69.
8. (e) Perry, M. C.; Burgess, K. Tetrahedron: Asymmetry 2003, 14, 951-961.
9. (f) César, V.; Bellemin-Laponnaz, S.; Gade, L. H. Chem. Soc. Rev. 2004, 33, 619-636.
10. (g) Crudden, C. M.; Allen, D. P. Coord. Chem. Rev. 2004, 248, 2247-2273.
11. (h) Scott, N. M.; Nolan, S. P. Eur. J. Inorg. Chem. 2005, 1815-1828.
12. (i) Hahn, F. E.; Jahnke, M. C. Angew. Chem., Int. Ed. 2008, 47, 3122-3172.
13. For reviews, see: (a) Bourrisou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39-91.
14. (b) de Frémont, P.; Marion, N.; Nolan, S. P. Coord. Chem. Rev. 2009, 253, 862-892.
15. For selected examples, see: (a) Viciu, M. S.; Grasa, G. A.; Nolan, S. P. Organometallics 2001, 20, 3607-3612.
16. (b) Grasa, G. A.; Viciu, M. S.; Huang, J.; Nolan, S. P. J. Org. Chem. 2001, 66, 7729-7737.
17. (c) Lee, S.; Hartwig, J. F. J. Org. Chem. 2001, 66, 3402-3415.
18. (d) Ma, Y.; Song, C.; Jiang, W.; Wu, Q.; Wang, Y.; Liu, X.; Andrus, M. B. Org. Lett. 2003, 5, 3317-3319.
19. (e) Altenhoff, G.; Goddard, R.; Lehmann, C. W.; Glorius, F. J. Am. Chem. Soc. 2004, 126, 15195-15201.
20. (f) Fleckenstein, C.; Roy, S.; Leuthäusser, S.; Plenio, H. Chem. Commun. 2007, 2870-2872.
21. (g) Kantchev, E. A. B.; O'Brien, C. J.; Organ, M. G. Angew. Chem., Int. Ed. 2007, 46, 2768-2813.
22. For reviews, see: (a) Lin, I. J. B.; Vasam, C. S. Comments Inorg. Chem. 2004, 25, 75-129.
23. (b) Garrison, J. C.; Youngs, W. J. Chem. Rev. 2005, 105, 3978-4008.
24. (c) Lin, I. J. B.; Vasam, C. S. Coord. Chem. Rev. 2007, 251, 642-670.
25. Chianese, A. R.; Zeglis, B. M.; Crabtree, R. H. Chem. Commun. 2004, 2176-2177.
26. Tudose, A.; Demonceau, A.; Delaude, L. J. Organomet. Chem. 2006, 691, 5356-5365.
27. Tudose, A.; Delaude, L.; André, B.; Demonceau, A. Tetrahedron Lett. 2006, 47, 8529-8533.
28. Duong, H. A.; Tekavec, T. N.; Arif, A. M.; Louie, J. Chem. Commun. 2004, 112-113.
29. Zhou, H.; Zhang, W.-Z.; Liu, C.-H.; Qu, J.-P.; Lu, X.-B. J. Org. Chem. 2008, 73, 8039-8044.
30. (a) Kayaki, H.; Ikarija, T. JP 2006-137733, 2006;
31. Chem. Abstr. 2006, 145, 27996.
32. (b) Bantu, B.; Pawar, G. M.; Decker, U.; Wurst, K.; Schmidt, A. M.; Buchmeiser, M. R. Chem. - Eur. J. 2009, 15, 3103-3109.
33. (c) Bantu, B.; Pawar, G. M.; Wurst, K.; Decker, U.; Schmidt, A. M.; Buchmeiser, M. R. Eur. J. Inorg. Chem. 2009, 1970-1976.
34. (a) Voutchkova, A. M.; Appelhans, L. N.; Chianese, A. R.; Crabtree, R. H. J. Am. Chem. Soc. 2005, 127, 17624-17625.
35. (b) Voutchkova, A. M.; Feliz, M.; Clot, E.; Eisenstein, O.; Crabtree, R. H. J. Am. Chem. Soc. 2007, 129, 12834-12846.
36. (a) Jan, D.; Delaude, L.; Simal, F.; Demonceau, A.; Noels, A. F. J. Organomet. Chem. 2000, 606, 55-64.
37. (b) Maj, A.; Delaude, L.; Demonceau, A.; Noels, A. F. J. Organomet. Chem. 2007, 692, 3048-3056.
38. (c) Sauvage, X.; Borguet, Y.; Noels, A. F.; Delaude, L.; Demonceau, A. Adv. Synth. Catal. 2007, 349, 255-265.
39. (d) Sauvage, X.; Borguet, Y.; Zaragoza, G.; Demonceau, A.; Delaude, L. Adv. Synth. Catal. 2009, 351, 441-455.
40. Delaude, L.; Demonceau, A.; Noels, A. F. Curr. Org. Chem. 2006, 10, 203-215.
41. Delaude, L.; Demonceau, A.; Noels, A. F. Chem. Commun. 2001, 986-987.
42. Ahr, M.; Thieuleux, C.; Copéret, C.; Fenet, B.; Basset, J.-M. Adv. Synth. Catal. 2007, 349, 1587-1591.
43. Delaude, L.; Szypa, M.; Demonceau, A.; Noels, A. F. Adv. Synth. Catal. 2002, 344, 749-756.
44. Delaude, L.; Delfosse, S.; Richel, A.; Demonceau, A.; Noels, A. F. Chem. Commun. 2003, 1526-1527.
45. Delaude, L.; Demonceau, A.; Wouters, J. Eur. J. Inorg. Chem. 2009, 1882-1891.
46. Dragutan, V.; Dragutan, I.; Delaude, L.; Demonceau, A. Coord. Chem. Rev. 2007, 251, 765-794.
47. Herrmann, W. A.; Köcher, C.; Goossen, L. J.; Artus, G. R. J. Chem - Eur. J. 1996, 2, 1627-1636.
48. Jafarpour, L.; Huang, J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 3760-3763.
49. Lo, C.; Cariou, R.; Fischmeister, C.; Dixneuf, P. H. Adv. Synth. Catal. 2007, 349, 546-550.
50. Ledoux, N.; Allaert, B.; Verpoort, F. Eur. J. Org. Chem. 2007, 5578-5583.
51. For reviews, see: (a) Kirmse, W. Eur. J. Org. Chem. 2005, 237-260.
52. (b) Delaude, L. Eur. J. Inorg. Chem. 2009, 1681-1699.
53. Blanrue, A.; Wilhelm, R. Synlett 2004, 2621-2623.
54. Sereda, O.; Blanrue, A.; Wilhelm, R. Chem. Commun. 2009, 1040-1042.
55. (a) Cuyas, J.; Miguel, D.; Pérez-Martínez, J. A.; Riera, V. Polyhedron 1992, 11, 2713-2716.
56. (b) Alvarez, B.; Miguel, D.; Pérez-Martinez, J. A.; Riera, V. J. Organomet. Chem. 1994, 474, 143-147.
57. We thank one of the anonymous reviewers for encouraging us to probe this simple aerobic route.
58. Ritter, T.; Hejl, A.; Wenzel, A. G.; Funk, T. W.; Grubbs, R. H. Organometallics 2006, 25, 5740-5745.
59. For a review, see: Galindo, A.; Miguel, D.; Perez, J. Coord. Chem. Rev. 1999, 193-195, 643-690.
60. For reviews, see: (a) Coucouvanis, D. Prog. Inorg. Chem. 1970, 11, 233-371.
61. (b) Eisenberg, R. Prog. Inorg. Chem. 1970, 12, 295-369.
62. (c) Coucouvanis, D. Prog. Inorg. Chem. 1979, 26, 301-469.
63. (d) Bums, R. P.; McCullough, F. P.; McAuliffe, C. A. Adv. Inorg. Chem. Radiochem. 1980, 23, 211-280.
64. (e) Hogarth, G. Prog. Inorg. Chem. 2005, 53, 71-561.
65. For recent examples, see: (a) Knight, E. R.; Cowley, A. R.; Hogarth, G.; Wilton-Ely, J. D. E. T. Dalton Trans. 2009, 607-609.
66. (b) Macgregor, M. J.; Hogarth, G.; Thompson, A. L.; Wilton-Ely, J. D. E. T. Organometallics 2009, 28, 197-208.
67. (c) Knight, E. R.; Leung, N. H.; Thompson, A. L.; Hogarth, G.; Wilton-Ely, J. D. E. T. Inorg. Chem. 2009, 48, 3866-3874.
68. (d) Knight, E. R.; Leung, N. H.; Lin, Y. H.; Cowley, A. R.; Watkin, D. J.; Thompson, A. L.; Hogarth, G.; Wilton-Ely, J. D. E. T. Dalton Trans. 2009, 3688-3697.
69. (a) Borer, L. L.; Kong, J. V. Inorg. Chim. Acta 1986, 122, 145-148.
70. (b) Borer, L. L.; Kong, J. V.; Keihl, P. A.; Forkey, D. M. Inorg. Chim. Acta 1987, 129, 223-226.
71. For reviews, see: (a) LeBozec, H.; Touchard, D.; Dixneuf, P. H. Adv. Organomet. Chem. 1989, 29, 163-247.
72. (b) Bennett, M. A. Coord. Chem. Rev. 1997, 166, 225-254.
73. (c) Therrien, B. Coord. Chem. Rev. 2009, 253, 493-519.
74. Allen, F. H.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. In International Tables for Crystallography; Prince, E., Ed.; Springer: Berlin, 2006; Vol. C, pp 790-811.
75. (a) Ziegler, M. L.; Weber, H.; Nuber, B.; Serhadle, O. Z. Naturforsch., Teil B 1987, 42, 1411-1418.
76. (b) Nagasawa, A.; Akiyama, I.; Mashima, S.; Nakayama, J. Heteroat. Chem. 1995, 6, 45-49.
77. (c) Fujihara, T.; Ohba, T.; Nagasawa, A.; Nakayama, J.; Yoza, K. Acta Crystallogr., Sect. C 2002, 58, o558-o559.
78. Kuhn, N.; Steimann, M.; Weyers, G. Z. Naturforsch., Teil B 1999, 54, 427-433.
79. (a) Sheldrick, W. S.; Schönberg, A.; Singer, E.; Eckert, P. Chem. Ber. 1980, 113, 3605-3609.
80. (b) Borer, L. L.; Kong, J. V.; Oram, D. E. Acta Crystallogr., Sect. C 1989, 45, 1169-1170.
81. (c) Kuhn, N.; Bohnen, H.; Henkel, G. Z. Naturforsch., Teil B 1994, 49, 1473-1480.
82. (d) Kuhn, N.; Niquet, E.; Steimann, M.; Walker, I. Z. Naturforsch., Teil B 1999, 54, 1181-1187.
83. (e) Akkurt, M.; Öztürk, S.; Küçükbay, H.; Orhan, E.; Büyülgüngör, O. Acta Crystallogr., Sect. E 2004, 60, o219-o221.
84. Nakayama, J.; Kitahara, T.; Sugihara, Y.; Sakamoto, A.; Ishii, A. J. Am. Chem. Soc. 2000, 122, 9120-9126.
85. Syed Mohamed, K.; Padma, D. K. Spectrochim. Acta, Part A 1985, 41, 725-728.
86. Furlani, C.; Luciani, M. L. Inorg. Chem. 1968, 7, 1586-1592.
87. Bennett, M. A.; Smith, A. K. J. Chem. Soc., Dalton Trans. 1974, 233-241.
88. Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structures; University of Göttingen: Göttingen (Germany), 1997.
89. Speck, A. L. PLATON, A Multipurpose Crystallographic Tool; Utrecht University: Utrecht (The Netherlands), 2005.