Stereoselective cyclometalation of planar Pro-chiral (η6- arene)tricarbonylchromium complexes with OC-6-[Ru(CO)2Cl 2]n

Organometallics

Volumn 26, Issue 17, 2007, Pages 4180-4196

  Hijazi, Akram ^a   Djukic, Jean Pierre ^a   Allouche, Lionel ^a   De Cian, André ^a   Pfeffer, Michel ^a   Le Goff, Xavier Frédéric ^b   Ricard, Louis ^b  

^a UNIVERSITÉ LOUIS PASTEUR   (France)

^b LABORATOIRE HÉTÉROÉLÉMENTS ET COORDINATION   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CHIRALITY; COMPLEXATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RUTHENIUM COMPOUNDS; STEREOSELECTIVITY; X RAY DIFFRACTION;

CYCLOMETALATION REACTION; ORTHO METALATION; STEREOSELECTIVE CYCLOMETALATION; TRICARBONYLCHROMIUM COMPLEXES;

ORGANOMETALLICS;

EID: 34548160219     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om070239p     Document Type: Article

References (149)

1. (a) Sokolov, V. I. Pure Appl. Chem. 1983, 55, 1837-1844.
2. (b) Sokolov, V. I.; Krushcheva, N. S.; Troitskaya, L. L.; Reutov, O. A. Dokl. Akad. Nauk. 1984, 274, 342-347.
3. (c) Troitskaya, L. L.; Sokolov, V. I. J. Organomet. Chem. 1985, 285, 389-393.
4. (d) Troitskaya, L. L.; Bulygina, L. A.; Sokolov, V. I. Izv. Akad. Nauk. Ser. Khim. 1993, 1799-1802.
5. (e) Malésieux, B.; Gruselle, M.; Troitskaya, L.; Sokolov, V. Tetrahedron: Asymmetry 1998, 9, 259-269.
6. (f) Ryabov, A.; Firsova, Y. N.; Goral, V. N.; Ryabova, E. S.; Shevelkova, A. N.; Troitskaya, L. L.; Demeschik, T. V.; Sokolov, V. I. Chem.-Eur. J. 1998, 4, 806-813.
7. (g) Mamedyarova, I. A.; Nefedova, M. N.; Sokolov, V. I. J. Organomet. Chem. 1996, 524, 181-186.
8. (h) Ryabov, A. D.; Panyashkina, I. M.; Polyakov, V. A.; Howard, J. A. K.; Kuz'mina, L. G.; Datt, M. S.; Sacht, C. Organometallics 1998, 17, 3615-3618.
9. (i) Roca, F. X.; Motevalli, M.; Richards, C. J. J. Am. Chem. Soc. 2005, 127, 2388-2389.
10. (a) Kirsch, S. F.; Overman, L. E. J. Am. Chem. Soc. 2005, 127, 2866-2867.
11. (b) Kirsch, S. F.; Overman, L. E.; Watson, M. P. J. Org. Chem. 2004, 69, 8101-8104.
12. (c) Lopez, C.; Caubet, A.; Perez, S.; Solans, X.; Font-Bardia, M. Chem. Commun. 2004, 540-541.
13. (d) Overman, L. E.; Owen, C. E.; Pavan, M. M.; Richards, C. J. Org. Lett. 2003, 5, 1809-1812.
14. (e) Anderson, C. E.; Overman, L. E. J. Am. Chem. Soc. 2003, 125, 12412-12413.
15. (f) Howell, J. A. S.; Yates, P. C.; Fey, N.; McArdle, P.; Cunningham, D.; Parsons, S.; Rankin, D. W. H. Organometallics 2002, 21, 5272-5286.
16. (g) Bolm, C.; Wenz, K.; Raabe, G. J. Organomet. Chem. 2002, 662, 23-33.
17. (h) Jones, G.; Richards, C. J. Organometallics 2001, 20, 1251-1254.
18. (i) Djukic, J. P.; Michon, C.; Maisse-François, A.; Allagapen, R.; Pfeffer, M.; Doetz, K. H.; de Cian, A.; Fischer, J. Chem.-Eur. J. 2000, 6, 1064-1077.
19. (j) Wu, Y.; Cui, X.; Zhou, N.; Song, M.; Yun, H.; Du, C.; Zhu, Y. Tetrahedron: Asymmetry 2000, 11, 4877-4883.
20. (k) Stevens, A. M.; Richards, C. J. Organometallics 1999, 18, 1346-1348.
21. (l) Sokolov, V. I.; Troitskaya, L. L.; Khrushchova, N. S. J. Organomet. Chem. 1983, 250, 439-446.
22. (m) Cohen, F.; Overman, L. E. Tetrahedron: Asymmetry 1998, 9, 3213-3222.
23. (n) Zhao, G.; Wang, Q. G.; Mak, T. C. W. Polyhedron 1998-1999, 18, 577-584.
24. (o) Zhao, G.; Wang, Q. G.; Mak, T. C. W. J. Organomet. Chem. 1999, 574, 311-317.
25. (p) Djukic. J. P.; Maisse, A.; Pfeffer, M. J. Organomet. Chem. 1998, 567, 65-74.
26. (q) Benito, M.; Lopez, C.; Solans, X.; Font-Bardia, M. Tetrahedron: Asymmetry 1998, 9, 4219-4238.
27. (r) Zhao, G.; Wang, Q. G.; Mak, T. C. W. J. Chem. Soc., Dalton Trans. 1998, 3785-3789.
28. (s) Hollis, T. K.; Overman, L. E. Tetrahedron Lett. 1997, 38, 8837-8840.
29. (t) Djukic, J. P.; Maisse, A.; Pfeffer, M.; de Cian, A.; Fischer, J. Organometallics 1997, 16, 657-667.
30. (u) Stevens, A. M.; Richards, C. J. Tetrahedron Lett. 1997, 38, 7805-7808.
31. (v) Lopez, C.; Bosque, R.; Solans, X.; Font-Bardia, M. Tetrahedron; Asymmetry 1996, 7, 2527-2530.
32. (w) Sokolov, V. I.; Troitskaya, L. L.; Rozhkova, T. I. Gazz. Chim. Ital. 1987, 117, 525-527.
33. (x) Sokolov, V. I.; Troitskaya, L. L.; Reutov, O. A. J. Organomet. Chem. 1977, 133, C28-C30.
34. (y) Troitskaya, L. L.; Sokolov, V. I.; Reutov, O. A. Dokl. Akad. Nauk. SSSR 1977, 236, 371-374.
35. (z) Sokolov, V. I.; Troitskaya, L. L.; Reutov, O. A. Dokl. Akad. Nauk. SSSR 1977, 237, 1376-1379.
36. (a) Peters, R.; Xin, Z. Q.; Fischer, D. F.; Schweizer, W. B. Organometallics 2006, 25, 2917-2920.
37. (b) Anderson, C. E.; Donde, Y.; Douglas, C. J.; Overman, L. E. J. Org. Chem. 2005, 70, 648-657.
38. (c) Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13.
39. (d) G. Zipp, Ph.D. Dissertation, University of California, Irvine, 2001; UMI microforms, Ann Arbor, no. 9993250.
40. (a) Djukic, J. P.; Berger, A.; Duquenne, M.; Pfeffer, M.; de Cian, A.; Kyritsakas-Gruber, N.; Vachon, J.; Lacour, J. Organometallics 2004, 23, 5757-5767.
41. (b) Wu, Y.; Yang, L.; Cui, X.; Du, C.; Zhu, Y. Tetrahedron: Asymmetry 2003, 14, 1073-1077.
42. (c) Berger, A.; Djukic, J. P.; Pfeffer, M.; de Cian, A.; Kyritsakas-Gruber, N.; Lacour, J.; Vial, L. Chem. Commun. 2003, 658-659.
43. (d) Berger, A.; Djukic, J. P.; Pfeffer, M.; Lacour, J.; Vial, L.; de Cian, A.; Kyritsakas-Gruber, N. Organometallics 2003, 22, 5243-5260.
44. (e) Wu, Y. J.; Cui, X. L.; Hou, J. J.; Yang, L. R.; Wang, M.; Du, C. X.; Zhu, Y. Acta Chim. Sin. 2000, 58, 871-875.
45. (f) Cui, X. L.; Wu, Y. J.; Du, C. X.; Yang, L. R.; Zhu, Y. Tetrahedron: Asymmetry 1999, 10, 1255-1262.
46. (g) Kuz'mina, L. G.; Strutchkov, Y. T.; Troitskaya, L. L.; Sokolov, V. I.; Reutov, O. A. Izv. Akad. Nauk. SSSR Ser. Khim. 1979, 1528-1534.
47. (a) Sokolov, V. I.; Nechaeva, K. S.; Reutov, O. A. J. Organomet. Chem. 1983, 253, C55-C58.
48. (b) Komatsu, T.; Noyoma, M.; Fujita, J. Bull. Chem. Soc. Jpn. 1981, 54, 186-189.
49. (a) Sokolov, V. I. J. Organomet. Chem. 1995, 500, 299-306.
50. (b) Sokolov, V. I.; Troitskaya, L. L. Chimia 1978, 32, 122-123.
51. (c) Sokolov, V. I.; Troitskaya, L. L.; Reutov, O. A. J. Organomet. Chem. 1979, 182, 537-546.
52. (a) Anderson, C. E.; Donde, Y.; Douglas, C. J.; Overman, L. E. J. Org. Chem. 2005, 70, 648-657.
53. (b) Kirsch, S. F.; Overman, L. E. J. Am. Chem. Soc. 2005, 127, 2866-2867.
54. (c) Moyano, A.; Rosol, M.; Moreno, R. M.; Lopez, C.; Maestro, M. A. Angew. Chem., Int. Ed. 2005, 44, 1865-1869.
55. Kirsch, S. F.; Overman, L. E.; Watson, M. P. J. Org. Chem. 2004, 69, 8101-8104.
56. (e) Overman, L. E.; Owen, C. E.; Pavan, M. M.; Richards, C. J. Org. Lett. 2003, 5, 1809-1812.
57. (f) Anderson, C. E.; Overman, L. E. J. Am. Chem. Soc. 2003, 125, 12412-12413.
58. (g) Overman, L. E.; Remarchuk, T. P. J. Am. Chem. Soc. 2002, 124, 12-13.
59. (h) Cohen, F.; Overman, L. E. Tetrahedron: Asymmetry 1998, 9, 3213-3222.
60. (i) Hollis, T. K.; Overman, L. Tetrahedron Lett. 1997, 38, 8837-8840.
61. (a) Faller, J. W.; Parr, J.; Lavoie, A. R. New J. Chem. 2003, 27, 899-901.
62. (b) Brunner, H.; Zwack, T.; Zabel, M.; Beck, W.; Böhm, A. Organometallics 2003, 22, 1741-1750.
63. (c) Brunner, H.; Klankermayer, J.; Zabel, M. Organometallics 2002, 21, 5746-5756.
64. (d) Robitzer, M.; Ritleng, V.; Sirlin, C.; Dedieu, A.; Pfeffer, M. C. R. Chim. 2002, 5, 467-472.
65. (e) Ritleng, V.; Bertani, P.; Pfeffer, M.; Sirlin, C.; Hirschinger, J. Inorg. Chem. 2001, 40, 5117-5122.
66. (f) Pfeffer, M. Organometallics 2000, 19, 2427.
67. (g) Brunner, H.; Zwack, T. Organometallics 2000, 19, 2423-2426.
68. (h) Brunner, H. Angew. Chem. 1999, 111, 1248-1263; Angew. Chem., Int. Ed. 1999, 38, 1194-1208.
69. (i) Brunner, H.; Oeschley, R.; Nuber, B. Inorg. Chem. 1995, 34, 3349-3351.
70. Hijazi, A.; Djukic, J. P.; Pfeffer, M.; Ricard, L.; Kyritsakas-Gruber, N.; Raya, J.; Bertani, P.; de Cian, A. Inorg. Chem. 2006, 45, 4589-4591.
71. (a) Pearson, P.; Kepert, C. M.; Deacon, G. B.; Spiccia, L.; Warden, A. C.; Skelton, B. W.; White, A. H. Inorg. Chem. 2004, 43, 683-691.
72. (b) Faure, M.; Saccavini, C.; Lavigne, G.; Trujillo, A.; Oelckers, B. Inorg. Synth. 2004, 34, 110-114.
73. (c) Hiraki, K.; Obayashi, Y.; Oki, Y. Bull. Chem. Soc. Jpn 1979, 52, 1372-1376.
74. (d) King, R. B.; Kapoor, P. N. Inorg. Chem. 1972, 11, 336-342.
75. (e) Colton, R.; Frathing, R. H. Aust. J. Chem. 1971, 24, 903-909.
76. (f) Cleare, M. J.; Griffith, W. P. Chem. Ind. 1967, 1705-1706.
77. (g) Cleare, M. J. Platinum Met. Rev. 1967, 11, 148-149.
78. (h) Collman, J. P.; Roper, W. R. J. Am. Chem. Soc. 1965, 87, 4008-4009.
79. (a) Hiraki, K.; Obayashi, Y.; Oki, Y. Bull. Chem. Soc. Jpn. 1979, 52, 1372-1376.
80. (b) Bruce, M. I.; Iqbal, M. Z.; Stone, F. G. A. J. Chem. Soc. A 1971, 2820-2828.
81. (a) Islam, S. M.; Saha, C. R. J. Mol. Catal. A 2004, 212, 131-140.
82. (b) Ferstl, W.; Sakodinskaya, I. K.: Beydoun-Sutter, N.; Le Borgne, G.; Pfeffer, M.; Ryabov, A. D. Organometallics 1997, 16, 411-418.
83. (c) Kimachi, S.; Satomi, R.; Miki, H.; Maeda, K.; Azumi, T.; Onishi, M. J. Phys. Chem. A 1997, 101, 345-349.
84. (d) Mukherjee, D. K.; Palit, B. K.; Saha, C. R. J. Mol. Catal. 1994, 88, 57-70.
85. (e) Mukherjee, D. K.; Palit, B. K.; Saha, C. R. J. Mol. Catal. 1994, 97, 19-30.
86. (f) Mul, W. P.; Elsevier, C. J.; Van Leijen, M.; Spaans, J. Organometallics 1991, 10, 251-255.
87. (g) Bruce, M. I.; Iqbal, M. Z.; Stone, F. G. A. J. Chem. Soc., Chem. Commun. 1970, 1325-1327.
88. (a) Cotts, R. M.; Hoch, M. J. R.; Sun, T.; Marker, J. T. J. Magn. Reson. 1989, 83, 252-266.
89. (b) Johnson, R. Prog. NMR Spectrosc. 1999, 34, 203-256.
90. (a) Wagner, G. W.; Hanson, B. E. Inorg. Chem. 1987, 26, 2019-2022.
91. (b) Oprunenko, Y.; Gloriosov, I.; Lyssenko, K.; Malyugina, S.; Mityuk, D.; Mstislavsky, V.; Günther, H.; von Firks, G.; Ebener, M. J. Organomet. Chem. 2002, 656, 27-42.
92. Yi, C. S.; Zeczycki, T. N.; Guzei, I. A. Organometallics 2006, 25, 1047-1051.
93. (a) Zhang, Q. F.; Adams, R. D.; Leung, W. H. Inorg. Chim. Acta 2006, 359, 978-983.
94. (b) Cariati, E.; Lucenti, E.; Pizzotti, M.; Roberto, D.; Ugo, R. Organometallics 1996, 15, 4122-4124.
95. (a) Akita, M.; Takahashi, Y.; Hikichi, S.; Moro-Oka, Y. Inorg. Chem. 2001, 40, 169-172.
96. (b) Burn, M. J.; Fickes, M. G.; Hartwig, J. F.; Hollander, F. J.; Bergman, R. G. J. Am. Chem. Soc 1993, 115, 5875-5876.
97. (a) Suresh, C. H.; Koga, N.; Gadre, S. R. Organometallics 2000, 19, 3008-3015.
98. (b) Pfletschinger, A.; Dargel, T. K.; Bats, J. W.; Schmalz, H.-G.; Koch, W. Chem. - Eur. J. 1999, 5, 537-545.
99. (c) Gambino, O.; Michelin-Lausarot, P.; Vaglio, G. A.; Valle, M.; Volpe, P.; Operti, L. Trans. Met. Chem. 1982, 7, 330-332.
100. (d) Lokshin, B. V.; Rusach, E. B.; Kaganovich, V. S.; Krivykh, V. V.; Artemov, A. N.; Sirotkin, N. I. Zh. Strukt. Khim. 1975, 16, 592-604.
101. (e) Lillya, C. P.; Sahajian, R. A. Inorg. Chem. 1971, 11, 889-891.
102. Throughout the present article this extended CIP sequence rule is used to assign the pS or the pR stereochemical descriptors to planar-chiral molecules. Readers are referred to the following references for more details: (a) Schlögl, K.; Fried, M. Monatsh. Chem. 1964, 95, 558-575.
103. (b) Schlögl, K.; Fried, M.; Falk, H. Monatsh. Chem. 1964, 95, 576-597.
104. (c) Cahn, R. S.; Ingold, C.; Prelog, V. Angew. Chem., Int. Ed. 1966, 385-415.
105. (d) Schlögl, K. Top. Stereochem. 1967, 7, 39-91.
106. F or IUPACs basic terminology of stereochemistry see: Moss, G. P. Pure Appl. Chem. 1996, 68, 2193-2222.
107. IUPAC Nomenclature of Inorganic Chemistry, Recommendation 1990; Leigh, G. J., Ed.; Blackwell Scientific Publications: Oxford, U.K., 1991.
108. Schlögl, K.; Fried, M. Monatsh. 1963, 94, 537-543.
109. The reader is referred to the structures with the following CCDC reference codes. LUQMOZ: Osintseva, S. V.; Dolgushin, F. M.; Petrovskii, P. V.; Shtel'tser, N. A.; Kreindlin, A. Z.; Rybin, L. V.; Rybinskaya, M. I. Izv. Akad. Nauk SSSR, Ser. Khim. 2002, 1610-1619.
110. VIGWIR: Osintseva, S. V.; Petrovskaya, E. A.; Rybin, L. V.; Kreindlin, A. Z.; Dolgushin, F. M.; Yanovsky, A. I.; Petrovskii, P. V.; Rybinskaya, M. I. Izv. Akad. Nauk SSSR Ser. Khim. 2000, 1616-1623.
111. See also: Zhang, Q. F.; Cheung, K. M.; Williams, I. D.; Leung, W. H. Eur. J. Inorg. Chem. 2005, 4780-4787.
112. Eaton, G. R.; Eaton, S. S. J. Am. Chem. Soc. 1975, 97, 235-236.
113. (a) Morley, J. A.; Woolsey, N. F. J. Org. Chem. 1992, 57, 6487-6495.
114. (b) Uemura, M.; Minami, T.; Hirotsu, K.; Hayashi, Y. J. Org. Chem. 1989, 54, 469-477.
115. (c) Desobry, V.; Kündig, E. P. Helv. Chim. Acta 1981, 64, 1288-1297.
116. (d) Strohmeier, W.; Mittnacht, H. Chem. Ber. 1960, 93, 2085-2086.
117. (a) Paley, R. S. Chem. Rev. 2002, 102, 1493-1523.
118. (b) Uemura, M.; Minami, T.; Hayashi, Y. J. Am. Chem. Soc. 1987, 109, 5277-5278.
119. (c) Uemura, M.; Kobayashi, T.; Isobe, K.; Minami, T.; Hayashi, Y. J. Org. Chem. 1986, 51, 2859-2863.
120. (a) Abbotto, A.; Bradamante, S.; Facchetti, A.; Pagani, G. A. J. Org. Chem. 2002, 67, 5753-5772.
121. (b) Ben Amar, H.; Le Nôtre, J.; Salem, M.; Kaddachi, M. T.; Dixneuf, P. H. J. Organomet. Chem. 2002, 662, 63-69.
122. (c) Ragaini, F.; Pizzotti, M.; Cenini, S.; Abbotto, A.; Pagani, G. A.; Demartin, F. J. Organomet. Chem. 1995, 489, 107-112.
123. Oprunenko, Y. F.; Malyugina, S. G.; Nesterenko, P.; Mityuk, D.; Malyshev, O. J. Organomet. Chem. 2000, 597, 42-47.
124. Kamikawa, K.; Sakamoto, T.; Tanaka, Y.; Uemura, M. J. Org. Chem. 2003, 68, 9356-9363.
125. (a) Muetterties, E. L. J. Am. Chem. Soc. 1969, 97, 1636-1643.
126. (b) Muetterties, E. L. J. Am. Chem. Soc. 1969, 91, 4115-4122.
127. Casanova, D.; Cirera, J.; Llunell, M.; Alemany, P.; Avnir, D.; Alvarez, S. J. Am. Chem. Soc. 2004, 126, 1755-1763.
128. Burdett, J. K.; Albright, T. A. Inorg. Chem. 1979, 18, 2112-2120.
129. (a) Jorgensen, C. K. Inorg. Chem. 1964, 3, 1201-1202.
130. (b) Pearson, R. G. Inorg. Chem. 1973, 12, 712-713.
131. (a) Soubra, C.; Oishi, Y.; Albright, T. A.; Fujimoto, H. Inorg. Chem. 2001, 40, 620-627.
132. (b) Lee, C. Y.; Wang, Y.; Liu, C. S. Inorg. Chem. 1991, 30, 3893-3899.
133. (c) Vancea, L.; Bennett, M. J.; Jones, C. E.; Smith, R. A.; Graham, W. A. G. Inorg. Chem. 1977, 16, 897-902.
134. (d) Tebbe, F. N.; Meakin, P.; Jesson, J. P.; Muetterties, E. L. J. Am. Chem. Soc. 1970, 92, 1068-1070.
135. (a) Debono, N.; Djakovitch, L.; Pinel, C. J. Organomet. Chem. 2006, 697, 741-747.
136. (b) Debono, N.; Besson, M.; Pinel, C.; Djakovitch, L. Tetrahedron Lett. 2004, 45, 2235-2238.
137. (c) Lee, A.; Kim, W.; Lee, J.; Hyeon, T.; Kim, B. M. Tetrahedron: Asymmetry 2004, 15, 2595-2598.
138. (d) Hanessian, S.; Yang, R. Y. Tetrahedron Lett. 1996, 37, 8997-9000.
139. (e) Nakamura, M.; Arai, M.; Nakamura, E. J. Am. Chem. Soc. 1995, 117, 1179-1180.
140. (f) Corey, E. J.; Wang, Z. Tetrahedron Lett. 1993, 34, 4001-4004.
141. (a) Flack, H. D.; Bernardinelli, G. J. Appl. Crystallogr. 2000, 33, 1143-1148.
142. (b) Flack, H. D. Acta Crystallogr. A 1983, A39, 876-881.
143. Fogassy, E.; Nogradi, M.; Kozma, D.; Egri, G.; Palovics, E.; Kiss, V. Org. Biomol. Chem. 2006, 4, 3011-3030.
144. Circular Dichroism, Principles and Applications, Second Edition; Berova, N., Nakanishi, K., Woody, R. W., Eds.; Wiley-VCH: New York, 2000.
145. Berger, A.; de Cian, A.; Djukic, J.-P.; Fischer, J.; Pfeffer, M. Organometallics 2001, 20, 3230-3240.
146. Davies, D. L.; Al-Duaij, O.; Fawcett, J.; Giardiello, M.; Hilton, S. T.; Russell, D. R. Dalton Trans. 2003, 4132-4138.
147. (a) Stejskal, E. O.; Tanner, J. E. J. Chem. Phys. 1965, 42, 288-292.
148. (b) Tanner, J. E. J. Chem. Phys. 1970, 52, 2523-2526.
149. Delsuc, M. A.; Malliavin, T. E. Anal. Chem. 1998, 70, 2146-2148.