Synthesis and application of new N-heterocyclic carbene ruthenium complexes in catalysis: A case study

Current Organic Chemistry

Volumn 10, Issue 2, 2006, Pages 203-215

  Delaude, Lionel ^a   Demonceau, Albert ^a   Noels, Alfred F ^a  

^a UNIVERSITY OF LIÈGE   (Belgium)

Author keywords

Atom Transfer Radical Addition; Cyclooctene; Imidazolinium salt; Norbornene; Ring Opening Metathesis; Ruthenium arene complexes; Styrene

Indexed keywords

ALKENE; ALKYL GROUP; BENZENE DERIVATIVE; BIPHENYL DERIVATIVE; CARBENE; CARBENOID; CARBON; CARBON TETRACHLORIDE; CHLORIDE; COORDINATION COMPOUND; DIAZOACETIC ACID ETHYL ESTER; DIMER; HETEROCYCLIC COMPOUND; IMIDAZOLE DERIVATIVE; INORGANIC SALT; LIGAND; NAPHTHALENE DERIVATIVE; NORBORNENE DERIVATIVE; PARA CYMENE; PHENYL GROUP; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POTASSIUM; RUTHENIUM COMPLEX; SODIUM DERIVATIVE; STYRENE;

CASE STUDY; CATALYSIS; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; CYCLOPROPANATION; EXPERIMENTAL DESIGN; METALLATION; PHOTOSYNTHESIS; PRECURSOR; REVIEW; RING OPENING METATHESIS POLYMERIZATION;

EID: 33645994862     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527206775192924     Document Type: Review

References (98)

1. Applied Homogeneous Catalysis with Organometallic Compounds; Second ed.; Cornils, B.; Herrmann, W. A., Eds.; Wiley-VCH: Weinheim, 2002.
2. Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: Sausalito, CA, 1999.
3. Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer: Berlin, 1998.
4. Bateson, J. H.; Mitchell, M. B. Organometallic Reagents in Organic Synthesis; Academic Press: London, 1994.
5. Organometallics in Synthesis; Schlosser, M., Ed.; Wiley: Chichester, 1994.
6. McQuillin, F. J.; Parker, D. G.; Stephenson, G. R. Transition Metal Organometallics for Organic Synthesis; Cambridge University Press: Cambridge, 1991.
7. Organic Synthesis via Organometallics; Dötz, K. H.; Hoffman, R. W., Eds.; Vieweg: Braunschweig, 1991.
8. Greenwood, N. N.; Earnshaw, A. Chemistry of the Elements; Pergamon Press: Oxford, 1984.
9. Ruthenium Catalysts and Fine Chemistry; Bruneau, C.; Dixneuf, P. H., Eds.; Topics in Organometallic Chemistry; Vol. 11; SpringerVerlag: Berlin, 2004.
10. Naota, T.; Takaya, H.; Murahashi, S.-I. Chem. Rev. 1998, 98, 2599-2660.
11. Friedrich, H. B. Platinum Met. Rev. 1999, 43, 94-102.
12. Bressan, M.; d'Alessandro, N.; Liberatore, L.; Morvillo, A. Coord. Chem. Rev. 1999, 185-186, 385-402.
13. Barf, G. A.; Sheldon, R. A. J. Mol. Catal. A: Chem. 1995, 102, 23-39.
14. Kalck, P.; Peres, Y.; Jerck, J. Adv. Organomet. Chem. 1991, 32, 121-146.
15. Ratovelomanana-Vidal, V.; Genet, J.-P. J. Organomet. Chem. 1998, 567, 163-172.
16. Matteoli, U.; Frediani, P.; Bianchi, M.; Botteghi, C.; Gladiali, S. J. Mol. Catal. A: Chem. 1981, 12, 265-319.
17. Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97-102.
18. Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003.
19. Ivin, K. J.; Mol, J. C. Olefin Metathesis and Metathesis Polymerization; Academic Press: San Diego, 1997.
20. Grubbs, R. H. Tetrahedron 2004, 60, 7117-7140.
21. Tmak, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
22. Frenzel, U.; Nuyken, O. J. Polym. Sci. A: Polym. Chem. 2002, 40, 2895-2916.
23. Metathesis Polymerization of Olefins and Polymerization of Alkynes; Imamoglu, Y., Ed.; NATO ASI Series C: Mathematical and Physical Sciences; Vol. 506; Kluwer: Dordrecht, 1998.
24. Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238.
25. McReynolds, M. D.; Dougherty, J. M.; Hanson, P. R. Chem. Rev. 2004, 104, 2239-2258.
26. Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-52.
27. Connon, S. J.; Blechert, S. Angew. Chem. Int. Ed. 2003, 42, 1900-1923.
28. Novel Metathesis Chemistry: Well-Defined Initiator Systems for Specialty Chemical Synthesis, Tailored Polymers and Advanced Material Applications; Imamoglu, Y.; Bencze, L., Eds.; NATO Science Series II. Mathematics, Physics and Chemistry; Vol. 122; Kluwer: Dordrecht, 2003.
29. Roy, R.; Das, S. K. Chem. Commun. 2000, 519-529.
30. Jørgensen, M.; Hadwiger, P.; Madsen, R.; Stüitz, A. E.; Wrodnigg, T. M. Curr. Org. Chem. 2000, 4, 568-588.
31. Schuster, M.; Blechert, S. Angew. Chem. Int. Ed. 1997, 36, 2036-2056.
32. Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067-2096.
33. Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012-3043.
34. Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731-1769.
35. Yi, C. S.; Liu, N. Synlett 1999, 281-287.
36. Wakatsuki, Y.; Yamazaki, H. J. Organomet. Chem. 1995, 500, 349-361.
37. Dixneuf, P. H.; Bruneau, C.; Derien, S. Pure Appl. Chem. 1998, 70, 1065-1070.
38. Maas, G. Chem. Soc. Rev. 2004, 33, 183-190.
39. Arduengo, A. J., III Acc. Chem. Res. 1999, 32, 913-921.
40. Bourrisou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39-91.
41. Herrmann, W. A. Angew. Chem. Int, Ed. 2002, 41, 1290-1309.
42. Jafarpour, L.; Nolan, S. P. Adv. Organomet. Chem. 2001, 46, 181-222.
43. Herrmann, W. A.; Köcher, C. Angew. Chem. Int. Ed. 1997, 36, 2162-2187.
44. Nair, V.; Bindu, S.; Sreekumar, V. Angew. Chem. Int. Ed. 2004, 43, 5130-5135.
45. Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534-541.
46. Cèsar, V.; Bellemin-Laponnaz, S.; Gade, L. H. Chem. Soc. Rev. 2004, 33, 619-636.
47. Delaude, L.; Demonceau, A.; Noels, A. F. Chem. Commun. 2001, 986-987.
48. Delaude, L.; Delfosse, S.; Richel, A.; Demonceau, A.; Noels, A. F. Chem. Commun. 2003, 1526-1527.
49. Richel, A.; Delfosse, S.; Cremasco, C.; Delaude, L.; Demonceau, A.; Noels, A. F. Tetrahedron Lett. 2003, 44, 6011-6015.
50. Delaude, L.; Delfosse, S.; Demonceau, A.; Richel, A.; Noels, A. F. In Novel Metathesis Chemistry: Well-Defined Initiator Systems for Specialty Chemical Synthesis, Tailored Polymers and Advanced Material Applications; Imamoglu, Y., Bencze, L., Eds.; NATO Science Series II. Mathematics, Physics and Chemistry; Vol. 122; Kluwer: Dordrecht, 2003; pp. 87-100.
51. Kuhn, N.; Kratz, T. Synthesis 1993, 561-562.
52. Hahn, F. E.; Wittenbecher, L.; Boesse, R.; Bläser, D. Chem. Eur. J. 1999, 5, 1931-1935.
53. Enders, D.; Breuer, K.; Raabe, G.; Runsink, J.; Teles, J. H.; Melder, J.-P.; Ebel, K.; Brode, S. Angew. Chem. Int. Ed. 1995, 34, 1021-1023.
54. Enders, D.; Breuer, K.; Kallfass, U.; Balensiefer, T. Synthesis 2003, 1292-1295.
55. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
56. Trnak, T. M.; Morgan, J. P.; Sanford, M. S.; Wihelm, T. E.; Scholl, M.; Choi, T.-L.; Ding, S.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 2546-2558.
57. Denk, K.; Sirsch, P.; Herrmann, W. A. J. Organomet. Chem. 2002, 649, 219-224.
58. Nyce, G. W.; Csihony, S.; Waymouth, R. M.; Hedrick, J. L. Chem. Eur. J. 2004, 20, 4073-4079.
59. Arduengo, A. J., III; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361-363.
60. Arduengo, A. J., III; Rasika Dias, H. V.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1992, 114, 5530-5534.
61. Harlow, K. J.; Hill, A. F.; Welton, T. Synthesis 1996, 697-698.
62. Voges, M. H.; Rømming, C.; Tilset, M. Organometallics 1999, 18, 529-533.
63. Fuller, J.; Carlin, R. T. J. Chem. Crystallogr. 1994, 24, 489-493.
64. Arduengo, A. J., III; Krafczyk, R.; Schmutzler, R.; Craig, H. A.; Goerlich, J. R.; Marshall, W. J.; Unverzagt, M. Tetrahedron 1999, 55, 14523-14534.
65. Huang, J.; Nolan, S. P. J. Am. Chem. Soc. 1999, 121, 9889-9890.
66. Delaude, L.; Szypa, M.; Demonceau, A.; Noels, A. F. Adv. Synth. Catal. 2002, 344, 749-756.
67. Tudose, A.; Mèret, M.; Maj, A.; Delaude, L.; Demonceau, A.; Noels, A. F. 2005, manuscript in preparation.
68. Lebedev, B.; Smirnova, N.; Kiparisova, Y.; Makovetsky, K. Makromol. Chem. 1992, 193, 1399-1411.
69. Ivin, K. J.; Laverty, D. T.; Rooney, J. J. Makromol. Chem. 1977, 178, 1545-1560.
70. Ivin, K. J.; Laverty, D. T.; Rooney, J. J. Makromol. Chem. 1978, 179, 253-258.
71. Stumpf, A. W.; Saive, E.; Demonceau, A.; Noels, A. F. Chem. Commun. 1995.
72. Ivin, K. J.; Laverty, D. T.; O'Donnell, J. H.; Rooney, J. J.; Stewart C. D. Makromol. Chem. 1979, 180, 1989-2000.
73. Greene, R. M. E.; Hamilton, J. G.; Ivin, K. J.; Rooney, J. J. Makromol. Chem. 1986, 187, 619-632.
74. Demonceau, A.; Stumpf, A. W.; Saive, E.; Noels, A. F. Macromolecules 1997, 30, 3127-3136.
75. Jan, D.; Delaude, L.; Simal, F.; Demonceau, A.; Noels, A. F. J. Organomet. Chem. 2000, 606, 55-64.
76. Lebedev, B.; Smirnova, N. Macromol. Chem. Phys. 1994, 195, 35-63.
77. Bencze, L.; Kraut-Vass, A.; Pròkai, L. Chem. Commun. 1985, 911-912.
78. Alvarez, P.; Girneno, J.; Lastra, P. Organometallics 2002, 21, 5678-5680.
79. Arduengo, A. J., III; Goerlich, J. R.; Krafczyk, R.; Marshall, W. J. Angew. Chem. Int. Ed. 1998, 37, 1963-1965.
80. Hitchcock, P. B.; Lappert, M. F.; Pye, P. L. Chem. Commun. 1977, 196-198.
81. Hitchcock, P. B.; Lappert, M. F.; Pye, P. L.; Thomas, S. J. Chem. Soc., Dalton Trans. 1979, 1929-1942.
82. Simal, F.; Jan, D.; Delaude, L.; Demonceau, A.; Spirlet, M.-R.; Noels, A. F. Can. J. Chem. 2001, 79, 529-535.
83. Simal, F.; Jan, D.; Demonceau, A.; Noels, A. F. Tetrahedron Lett. 1999, 76, 1653-1656.
84. Simal, F.; Demonceau, A.; Noels, A. F. Tetrahedron Lett. 1998, 39, 3493-3496.
85. Noels, A. F.; Demonceau, A.; Jan, D. Russ. Chem. Bull. 1999, 48, 1206-1211.
86. Noels, A. F.; Demonceau, A. J. Phys. Org. Chem. 1998, 11, 602-609.
87. Simal, F.; Demonceau, A.; Noels, A. F.; Knowles, D. R. T.; O'Leary, S.; Maitlis, P. M.; Gusev, O. J. Organomet. Chem. 1998, 558, 163-170.
88. Noels, A. F.; Demonceau, A.; Carlier, E.; Hubert, A. J.; Márquez-Silva, R.-L.; Sánchez-Delgado, R. A. Chem. Commun. 1988, 783-784.
89. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides; Wiley: New York, 1998.
90. Munslow, I. J.; Gillespie, K. M.; Deeth, R. J.; Scott, P. Chem. Commun. 2001, 1638-1639.
91. Nishiyama, H.; Itoh, Y.; Sugawara, Y.; Matsumoto, H.; Aoki, K.; Itoh, K. Bull. Chem. Soc. Jpn. 1995, 68, 1247-1262.
92. Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Adv. Synth. Catal. 2001, 343, 79-88.
93. Díaz-Requejo, M. M.; Belderrain, T. R.; Trofimenko, S.; Pérez, P. J. J. Am. Chem. Soc. 2001, 123, 3167-3168.
94. Díaz-Requejo, M. M.; Caballero, A.; Belderraín, T. R.; Nicasio, M. C.; Trofimenko, S.; Pérez, P. J. J. Am. Chem. Soc. 2002, 124, 978-983.
95. Fructos, M. R.; Belderraín, T. R.; Nicasio, M. C.; Nolan, S. P.; Kaur, H.; Díaz-Requejo, M. M.; Pérez, P. J. J. Am. Chem. Soc. 2004, 126, 10846-10847.
96. Delfosse, S.; Richel, A.; Delaude, L.; Demonceau, A.; Noels, A. F. 2005, manuscript in preparation.
97. Simal, F.; Demonceau, A.; Noels, A. F. Tetrahedron Lett. 1999, 40, 5689-5693.
98. Simal, F.; Wlodarczak, L.; Demonceau, A.; Noels, A. F. Eur. J. Org. Chem. 2001, 2689-2695.