Modulating the steric, electronic, and catalytic properties of Cp* ruthenium half-sandwich complexes with β-diketiminato ligands

Organometallics

Volumn 30, Issue 22, 2011, Pages 6119-6132

  Phillips, Andrew D ^a,b   Thommes, Katrin ^a   Scopelliti, Rosario ^a   Gandolfi, Claudio ^c   Albrecht, Martin ^b,c   Severin, Kay ^a   Schreiber, Dominique F ^b   Dyson, Paul J ^a  

^a EPFL   (Switzerland)

^b UNIVERSITY COLLEGE DUBLIN   (Ireland)

^c UNIVERSITY OF FRIBOURG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ATOM TRANSFER RADICAL ADDITION; CATALYTIC PROPERTIES; DIKETIMINATES; ELECTRON-DONATING; ELECTRON-DONATING SUBSTITUENTS; ELECTRON-WITHDRAWING SUBSTITUENTS; HALF-SANDWICH COMPLEXES; LIGAND SUBSTITUTION; REDUCTION-OXIDATION; RUTHENIUM COMPLEXES; SINGLE CRYSTAL X-RAY DIFFRACTION; SOLUTION NMR; STRUCTURAL DIFFERENCES; TOLUENE SULFONYL CHLORIDE; TRIFLUOROMETHYL GROUP; TURNOVER RATE; UV VISIBLE SPECTROSCOPY;

CYCLIC VOLTAMMETRY; CYCLIZATION; ELECTRONS; ETHERS; FREE RADICAL REACTIONS; LIGANDS; RUTHENIUM; RUTHENIUM COMPOUNDS; STYRENE; SUBSTRATES; ULTRAVIOLET VISIBLE SPECTROSCOPY; X RAY DIFFRACTION;

CHLORINE COMPOUNDS;

EID: 81755168935     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om2006479     Document Type: Article

References (137)

1. Grubbs, R. H. Introduction. In Handbook of Metathesis; Grubbs, R. H., Ed. Wiley-VCH: Weinheim, Germany, 2003; Vol. 1, pp 1-3.
2. Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2000, 34, 18-29
3. Kakiuchi, F. J. Synth. Org. Chem. 2004, 62, 14-26
4. Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826-834
5. Kitamura, M.; Noyori, R. Hydrogenation and Transfer Hydrogenation. In Ruthenium in Organic Synthesis; Murahasi, S.-I., Ed.; Wiley-VCH: Weinheim, Germany, 2004; pp 3-52.
6. Naota, T.; Takaya, H.; Murahashi, S. I. Chem. Rev. 1998, 98, 2599-2660
7. Griffith, W. P. Ruthenium Oxidation Complexes; Their Uses as Homogenous Organic Catalysts; Springer: Heidelberg, Germany, 2011; Vol. 34.
8. Murahashi, S.-I.; Komiya, N. Ruthenium-catalyzed Oxidation of Alkenes, Alcohols, Amines, Amides, beta-Lactams, Phenols, and Hydrocarbons. In Modern Oxidation Methods; Bäckvall, J.-E., Ed.; Wiley-VCH: Weinheim, Germany, 2004; pp 165-192.
9. Mohamed, A. A. Coord. Chem. Rev. 2010, 254, 1918-1947
10. Kitamura, M.; Hsiao, Y.; Noyori, R.; Takaya, H. Tetrahedron Lett. 1987, 28, 4829-4832
11. Ikariya, T.; Murata, K.; Noyori, R. Org. Biomol. Chem. 2006, 4, 393-406
12. Edelmann, F. T. Adv. Organomet. Chem. 2008, 57, 183-352
13. Bourget-Merle, L.; Lappert, M. F.; Severn, J. R. Chem. Rev. 2002, 102, 3031-3065
14. Hardman, N. J.; Eichler, B. E.; Power, P. P. Chem. Commun. 2000, 1991-1992
15. Cui, C. M.; Roesky, H. W.; Schmidt, H. G.; Noltemeyer, M.; Hao, H. J.; Cimpoesu, F. Angew. Chem., Int. Ed. 2000, 39, 4274-4276
16. Driess, M.; Yao, S. H.; Brym, M.; van Wullen, C. Angew. Chem., Int. Ed. 2006, 45, 6730-6733
17. Hill, M. S.; Hitchcock, P. B.; Pongtavornpinyo, R. Angew. Chem., Int. Ed. 2005, 44, 4231-4235
18. Holland, P. L. Acc. Chem. Res. 2008, 41, 905-914
19. Chai, J. F.; Zhu, H. P.; Stuckl, A. C.; Roesky, H. W.; Magull, J.; Bencini, A.; Caneschi, A.; Gatteschi, D. J. Am. Chem. Soc. 2005, 127, 9201-9206
20. Cramer, C. J.; Tolman, W. B. Acc. Chem. Res. 2007, 40, 601-608
21. Hayes, P. G.; Piers, W. E.; McDonald, R. J. Am. Chem. Soc. 2002, 124, 2132-2133
22. Mindiola, D. J. Angew. Chem., Int. Ed. 2009, 48, 6198-6200
23. Wang, Y. Z.; Quillian, B.; Wei, P. R.; Wang, H. Y.; Yang, X. J.; Xie, Y. M.; King, R. B.; Schleyer, P. V.; Schaefer, H. F.; Robinson, G. H. J. Am. Chem. Soc. 2005, 127, 11944-11945
24. Laitar, D. S.; Mathison, C. J. N.; Davis, W. M.; Sadighi, J. P. Inorg. Chem. 2003, 42, 7354-7356
25. Andres, R.; de, J. E.; de, l. M. F. J.; Flores, J. C.; Gomez, R. J. Organomet. Chem. 2005, 690, 939-943
26. Kakaliou, L.; Scanlon, W. J.; Qian, B. X.; Baek, S. W.; Smith, M. R.; Motry, D. H. Inorg. Chem. 1999, 38, 5964-5977
27. Tomson, N. C.; Yan, A.; Arnold, J.; Bergman, R. G. J. Am. Chem. Soc. 2008, 130, 11262-11263
28. Tonzetich, Z. J.; Jiang, A. J.; Schrock, R. R.; Müller, P. Organometallics 2007, 26, 3771-3783
29. Chiong, H. A.; Daugulis, O. Organometallics 2006, 25, 4054-4057
30. Shimokawa, C.; Itoh, S. Inorg. Chem. 2005, 44, 3010-3012
31. Dias, H. V. R.; Flores, J. A. Inorg. Chem. 2007, 46, 5841-5843
32. Carrera, N.; Savjani, N.; Simpson, J.; Hughes, D. L.; Bochmann, M. Dalton Trans. 2011, 40, 1016-1019
33. Venugopal, A.; Ghosh, M. K.; Jurgens, H.; Tornroos, K. W.; Swang, O.; Tilset, M.; Heyn, R. H. Organometallics 2010, 29, 2248-2253
34. Tian, X.; Goddard, R.; Porschke, K. R. Organometallics 2006, 25, 5854-5862
35. Fekl, U.; Goldberg, K. I. J. Am. Chem. Soc. 2002, 124, 6804-6805
36. Fekl, U.; Goldberg, K. I. Adv. Inorg. Chem. 2003, 54, 259-320
37. Fekl, U.; Kaminsky, W.; Goldberg, K. I. J. Am. Chem. Soc. 2001, 123, 6423-6424
38. Fekl, U.; Kaminsky, W.; Goldberg, K. I. J. Am. Chem. Soc. 2003, 125, 15286-15287
39. Budzelaar, P. H. M.; Moonen, N. N. P.; de Gelder, R.; Smits, J. M. M.; Gall, A. W. Eur. J. Inorg. Chem. 2000, 753-769
40. Geier, S. J.; Stephan, D. W. Chem. Commun. 2008, 2779-2781
41. Bernskoetter, W. H.; Lobkovsky, E.; Chirik, P. J. Organometallics 2005, 24, 4367-4373
42. Bernskoetter, W. H.; Lobkovsky, E.; Chirik, P. J. Organometallics 2005, 24, 6250-6259
43. Zhang, J.; Ke, Z.; Bao, F.; Long, J.; Gao, H.; Zhu, F.; Wu, Q. J. Mol. Catal. A: Chem. 2006, 249, 31-39
44. Zhou, M.-S.; Huang, S.-P.; Weng, L.-H.; Sun, W.-H.; Liu, D.-S. J. Organomet. Chem. 2003, 665, 237-245
45. Yuan, S.; Zhang, L.; Liu, D.; Sun, W.-H. Macromol. Res. 2010, 18, 690-694
46. Zhang, D.; Jin, G.-X.; Weng, L.-H.; Wang, F. Organometallics 2004, 23, 3270-3275
47. Xue, M.; Jiao, R.; Zhang, Y.; Yao, Y. M.; Shen, Q. Eur. J. Inorg. Chem. 2009, 4110-4188
48. Van, M. W. J.; Duchateau, R.; Koning, C. E.; Gruter, G.-J. M. Macromolecules 2005, 38, 7306-7313
49. Smith, K. M. Curr. Org. Chem. 2006, 10, 955-963
50. McGuinness, D. S. Cr Complexes of Nitrogen Donor Ligands for Olefin Oligomerisation and Polymerisation. In Olefin Upgrading Catalysis by Nitrogen-based Metal Complexes I; Campora, J.; Giambastiani, G., Eds.; Springer: Amsterdam: 2011; Vol. 35, pp 1-26.
51. Guan, B.; Xing, D.; Cai, G.; Wan, X.; Yu, N.; Fang, Z.; Yang, L.; Shi, Z. J. Am. Chem. Soc. 2005, 127, 18004-18005
52. Spielmann, J.; Buch, F.; Harder, S. Angew. Chem., Int. Ed. 2008, 47, 9434-9438
53. Lazarov, B. B.; Hampel, F.; Hultzsch, K. C. Z. Anorg. Allg. Chem. 2007, 633, 2367-2373
54. Badiei, Y. M.; Dinescu, A.; Dai, X.; Palomino, R. M.; Heinemann, F. W.; Cundari, T. R.; Warren, T. H. Angew. Chem., Int. Ed. 2008, 47, 9961-9964
55. Biyikal, M.; Loehnwitz, K.; Meyer, N.; Dochnahl, M.; Roesky, P. W.; Blechert, S. Eur. J. Inorg. Chem. 2010, 1070-1081
56. Moreno, A.; Pregosin, P. S.; Laurenczy, G.; Phillips, A. D.; Dyson, P. J. Organometallics 2009, 28, 6432-6441
57. Phillips, A. D.; Laurenczy, G.; Scopelliti, R.; Dyson, P. J. Organometallics 2007, 26, 1120-1122
58. Phillips, A. D.; Zava, O.; Scopelitti, R.; Nazarov, A. A.; Dyson, P. J. Organometallics 2010, 29, 417-427
59. Rauchfuss, T. Inorg. Synth. 2010, 35
60. Carey, D. T.; Cope-Eatough, E. K.; Vilaplana-Mafe, E.; Mair, F. S.; Pritchard, R. G.; Warren, J. E.; Woods, R. J. Dalton Trans. 2003, 1083-1093
61. Li, Y. F.; Jiang, L.; Wang, L. Y.; Gao, H. Y.; Zhu, F. M.; Wu, Q. Appl. Organomet. Chem. 2006, 20, 181-186
62. Phillips, A. D.; Dyson, P. J. Unpublished results.
63. Fairchild, R. M.; Holman, K. T. Organometallics 2008, 27, 1823-1833
64. Fan, L.; Turner, M. L.; Hursthouse, M. B.; Malik, K. M. A.; Gusev, O. V.; Maitlis, P. M. J. Am. Chem. Soc. 1994, 116, 385-386
65. Fan, L.; Wei, C.; Aigbirhio, F. I.; Turner, M. L.; Gusev, O. V.; Morozova, L. N.; Knowles, D. R. T.; Maitlis, P. M. Organometallics 1996, 15, 98-104
66. Kölle, U.; Kang, B.-S.; Thewalt, U. J. Organomet. Chem. 1990, 386, 267-273
67. Yamamoto, Y.; Arakawa, T.; Itoh, K. Organometallics 2004, 23, 3610-3614
68. Kogut, E.; Wiencko, H. L.; Zhang, L.; Cordeau, D. E.; Warren, T. H. J. Am. Chem. Soc. 2005, 127, 11248-11249
69. Melzer, M. M.; Jarchow-Choy, S.; Kogut, E.; Warren, T. H. Inorg. Chem. 2008, 47, 10187-10189
70. Chang, S.; Jones, L.; Wang, C.; Henling, L. M.; Grubbs, R. H. Organometallics 1998, 17, 3460-3465
71. Ding, F.; Sun, Y. G.; Monsaert, S.; Drozdzak, R.; Dragutan, I.; Dragutan, V.; Verpoort, F. Curr. Org. Synth. 2008, 5, 291-304
72. Huang, H.; Hughes, R. P.; Rheingold, A. L. Polyhedron 2008, 27, 734-738
73. Koelle, U. Chem. Rev. 1998, 98, 1313-1334
74. Nagashima, H.; Kondo, H.; Hayashida, T.; Yamaguchi, Y.; Gondo, M.; Masuda, S.; Miyazaki, K.; Matsubara, K.; Kirchner, K. Coord. Chem. Rev. 2003, 245, 177-190
75. Nagashima, H.; Gondo, M.; Masuda, S.; Kondo, H.; Yamaguchi, Y.; Matsubara, K. Chem. Commun. 2003, 442-443
76. Ahlemann, J. T.; Kunzel, A.; Roesky, H. W.; Noltemeyer, M.; Markovskii, L.; Schmidt, H. G. Inorg. Chem. 1996, 35, 6644-6645
77. Ahlemann, J. T.; Roesky, H. W.; Murugavel, R.; Parisini, E.; Noltemeyer, M.; Schmidt, H. G.; Muller, O.; HerbstIrmer, R.; Markovskii, L. N.; Shermolovich, Y. G. Chem. Ber. 1997, 130, 1113-1121
78. Ahlemann, J. T.; Roesky, H. W.; Noltemeyer, M.; Schmidt, H. G.; Markovsky, L. N.; Shermolovich, Y. G. J. Fluorine Chem. 1998, 87, 87-90
79. Dieck, H. T.; Kollvitz, W.; Kleinwachter, I. Inorg. Chem. 1984, 23, 2685-2691
80. Dieck, H. T.; Kollvitz, W.; Kleinwachter, I. Organometallics 1986, 5, 1449-1457
81. Nieuwenhuis, H. A.; Stufkens, D. J.; McNicholl, R. A.; Alobaidi, A. H. R.; Coates, C. G.; Bell, S. E. J.; McGarvey, J. J.; Westwell, J.; George, M. W.; Turner, J. J. J. Am. Chem. Soc. 1995, 117, 5579-5585
82. Aarnts, M. P.; Wilms, M. P.; Stufkens, D. J.; Baerends, E. J.; Vlcek, A. Organometallics 1997, 16 (10) 2055-2062
83. Kölle, U.; Raabe, G. Angew. Chem., Int. Ed. 1993, 32, 1294-1294
84. Saunders, G. C. J. Fluorine Chem. 2010, 131, 1187-1191
85. Chopra, D.; Row, T. N. G. Cryst. Eng. Commun. 2011, 13, 2175-2186
86. Kalinina, D.; Dares, C.; Kaluarachchi, H.; Potvin, P. G.; Lever, A. B. P. Inorg. Chem. 2008, 47, 10110-10126
87. Kharasch, M. S.; Jensen, E. V.; Urry, W. H. Science 1945, 102, 128-128
88. Matyjaszewski, K. Curr. Org. Chem. 2002, 6, 67-82
89. Clark, A. J. Chem. Soc. Rev. 2002, 31, 1-11
90. Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519-564
91. Minisci, F. Acc. Chem. Res. 1975, 8, 165-171
92. Matsumoto, H.; Nakano, T.; Nagai, Y. Tetrahedron Lett. 1973, 5147-5150
93. Severin, K. Curr. Org. Chem. 2006, 10, 217-224
94. Delaude, L.; Demonceau, A.; Noels, A. F. Ruthenium-promoted radical processes toward fine chemistry. In Ruthenium Catalysts and Fine Chemistry; Springer-Verlag: Berlin, 2004; Vol. 11, pp 155-171.
95. Eckenhoff, W. T.; Pintauer, T. Catal. Rev.-Sci. Eng. 2010, 52, 1-59
96. Pintauer, T.; Matyjaszewski, K. Chem. Soc. Rev. 2008, 37, 1087-1097
97. Gossage, R. A.; Van De Kuil, L. A.; Van Koten, G. Acc. Chem. Res. 1998, 31, 423-431
98. Borguet, Y.; Richel, A.; Delfosse, S.; Leclerc, A.; Delaude, L.; Demonceau, A. Tetrahedron Lett. 2007, 48, 6334-6338
99. Quebatte, L.; Haas, M.; Solari, E.; Scopelliti, R.; Nguyen, Q. T.; Severin, K. Angew. Chem., Int. Ed. 2005, 44, 1084-1088
100. Lundgren, R. J.; Rankin, M. A.; McDonald, R.; Stradiotto, M. Organometallics 2008, 27, 254-258
101. Quebatte, L.; Scopelliti, R.; Severin, K. Eur. J. Inorg. Chem. 2005, 3353-3358
102. Simal, F.; Wlodarczak, L.; Demonceau, A.; Noels, A. F. Tetrahedron Lett. 2000, 41, 6071-6074
103. Tutusaus, O.; Delfosse, S.; Demonceau, A.; Noels, A. F.; Vinas, C.; Teixidor, F. Tetrahedron Lett. 2003, 44, 8421-8425
104. Tutusaus, O.; Vinas, C.; Nunez, R.; Teixidor, F.; Demonceau, A.; Delfosse, S.; Noels, A. F.; Mata, I.; Molins, E. J. Am. Chem. Soc. 2003, 125, 11830-11831
105. Terasawa, J. I.; Kondo, H.; Matsumoto, T.; Kirchner, K.; Motoyama, Y.; Nagashima, H. Organometallics 2005, 24, 2713-2721
106. Motoyama, Y.; Hanada, S.; Niibayashi, S.; Shimamoto, K.; Takaoka, N.; Nagashima, H. Tetrahedron 2005, 61, 10216-10226
107. Motoyama, Y.; Gondo, M.; Masuda, S.; Iwashita, Y.; Nagashima, H. Chem. Lett. 2004, 33, 442-443
108. Opstal, T.; Verpoort, F. Tetrahedron Lett. 2002, 43, 9259-9263
109. Bull, J. A.; Hutchings, M. G.; Lujan, C.; Quayle, P. Tetrahedron Lett. 2008, 49, 1352-1356
110. Lee, B. T.; Schrader, T. O.; Martin-Matute, B.; Kauffman, C. R.; Zhang, P.; Snapper, M. L. Tetrahedron 2004, 60, 7391-7396
111. De Clercq, B.; Verpoort, F. J. Organomet. Chem. 2003, 672, 11-16
112. Opstal, T.; Verpoort, F. New J. Chem. 2003, 27, 257-262
113. Tallarico, J. A.; Malnick, L. M.; Snapper, M. L. J. Org. Chem. 1999, 64, 344-345
114. Simal, F.; Demonceau, A.; Noels, A. F. Tetrahedron Lett.s 1999, 40, 5689-5693
115. Richel, A.; Delfosse, S.; Cremasco, C.; Delaude, L.; Demonceau, A.; Noels, A. F. Tetrahedron Lett. 2003, 44, 6011-6015
116. Wolf, J.; Thommes, K.; Briel, O.; Scopelliti, R.; Severin, K. Organometallics 2008, 27, 4464-4474
117. Dutta, B.; Scopelliti, R.; Severin, K. Organometallics 2008, 27, 423-429
118. Motoyama, Y.; Hanada, S.; Shimamoto, K.; Nagashima, H. Tetrahedron 2006, 62, 2779-2788
119. Quebatte, L.; Scopelliti, R.; Severin, K. Angew. Chem., Int. Ed. 2004, 43, 1520-1524
120. Richel, A.; Demonceau, A.; Noels, A. F. Tetrahedron Lett. 2006, 47 (13) 2077-2081
121. Quebatte, L.; Thommes, K.; Severin, K. J. Am. Chem. Soc. 2006, 128 (23) 7440-7441
122. Thommes, K.; Fernandez-Zumel, M. A.; Buron, C.; Godinat, A.; Scopelliti, R.; Severin, K. Eur. J. Org. Chem. 2011, 249-255
123. Fernandez-Zumel, M. A.; Thommes, K.; Kiefer, G.; Sienkiewicz, A.; Pierzchala, K.; Severin, K. Chem. Eur. J. 2009, 15, 11601-11607
124. Thommes, K.; Kiefer, G.; Scopelliti, R.; Severin, K. Angew. Chem., Int. Ed. 2009, 48, 8115-8119
125. Thommes, K.; Icli, B.; Scopelliti, R.; Severin, K. Chem. Eur. J. 2007, 13, 6899-6907
126. Kamigata, N.; Shimizu, T. Rev. Heteroat. Chem. 1997, 17, 1-50
127. Ram, R. N.; Kumar, N. Tetrahedron Lett. 2008, 49, 799-802
128. Ram, R. N.; Charles, I. Chem. Commun. 1999, 2267-2268
129. Bieniek, M.; Michrowska, A.; Usanov, D. L.; Grela, K. Chem. Eur. J. 2008, 14, 806-818
130. Shriver, D. F.; Drezdzon, M. A. The Manipulation of Air-Sensitive Compounds; Wiley-Interscience: New York, 1986.
131. Komiya, S. Synthesis of Organometallic Compounds: A Practical Guide; Wiley-Interscience: New York, 1997.
132. Tilley, T. D.; Grubbs, R. H.; Bercaw, J. E. Organometallics 1984, 3, 274-278
133. Laitar, D. S.; Mathison, C. J. N.; Davis, W. M.; Sadighi, J. P. Inorg. Chem. 2003, 42, 7354-7356
134. Li, Y.; Jiang, L.; Wang, L.; Gao, H.; Zhu, F.; Wu, Q. Appl. Organomet. Chem. 2006, 20, 181-186
135. Li, Y.; Gao, H.; Wu, Q. J. Polym. Sci., Part A: Polym. Chem. 2007, 46, 93-101
136. Hill, M. S.; Pongtavornpinyo, R.; Hitchcock, P. B. Chem. Commun. 2006, 3720-3722
137. Dyson, P. J.; McIndoe, J. S. Inorg. Chim. Acta 2003, 354, 68-74