Heterobimetallic Cr-Mn complexes of fused arenes: Chromium-templated benzannulation of a cymanthrene-type metal carbene and haptotropic metal migration along a dibenzo[c,e]indene platform

Organometallics

Volumn 28, Issue 10, 2009, Pages 3004-3011

  Offner, Julien Dubarle ^a   Fröhliche, Roland ^b   Kataeva, Olga ^b   Rose Munch, Françoise ^c   Rose, Eric ^c   Dötz, Karl Heinz ^a  

^a UNIVERSITY OF BONN   (Germany)

^b UNIVERSITY OF MÜNSTER   (Germany)

^c Université Pierre et Marie Curie   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BENZANNULATION; CARBENE; CYCLOPENTADIENYL RINGS; DIASTEREOMERS; FIRST ORDER KINETICS; HAPTOTROPIC METAL MIGRATION; HETERO BIMETALLIC COMPLEXES; HETEROBIMETALLIC; METAL CARBENE; METAL CENTERS; NMR STUDIES; TEMPLATED;

CHROMIUM; COORDINATION REACTIONS; MANGANESE; MANGANESE COMPOUNDS; METALS;

CHROMIUM COMPOUNDS;

EID: 66249128285     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om900090q     Document Type: Article

References (119)

1. For reviews, see: (a) McQuillin, F. J.; Parker, D. G.; Stephenson, G. R. Transition Metal Organometallics for Organic Synthesis; Cambridge University Press: Cambridge, U.K., 1991.
2. (b) Morris, M. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Labinger, J. A., Winter, M. J., Vol.Eds.; Pergamon: Oxford, U.K., 1995; Vol.5, Chapter 8, p 471.
3. (c) Kündig, E. P. Topics in Organometalllic Chemistry; Springer: Berlin, Germany, 2004; Vol.7.
4. For reviews about chromium complexes, see: (a) Rose-Munch, F.; Rose, E. In Modern Arene Chemistry; Astruc, D., Ed.; Wiley-VCH: New York, 2002; Chapter 11, p 368.
5. (b) Rose-Munch, F.; Rose, E. Eur. J. Inorg. Chem. 2002, 1269.
6. (c) Kündig, E. P.; Pache, S. H. Arene Organometallic Complexes of Chromium, Molybdenum and Tungsten. In Science of Synthesis; Imamoto, T., Ed.; Thieme: Stuttgart, Germany, 2002; Vol.2, p 155.
7. (d) McGlinchey, M. J.; Ortin, Y.; Seward, C. M. Chromium Compounds with CO or Isocyanides. In Comprehensive Organometallic Chemistry III; Crabtree, R. H., Mingos, D. M. P., Eds.; Elsevier Science: Oxford, U.K., 2006; Vol.5, p 201.
8. (a) Mahaffy, C. A. L.; Pauson, P. L. Inorg. Synth. 1979, 19, 154.
9. (b) Desobry, V.; Kündig, E. P. Helv. Chim. Acta 1981, 64, 1288.
10. (c) Kündig, E. P.; Grivet, C.; Spichiger, S. J. Organomet. Chem. 1987, 332, C13.
11. (d) Zhang, S.; Shen, J. K.; Basolo, F.; Ju, T. D.; Lang, R. F.; Kiss, G.; Hoff, C. D. Organometallics 1994, 13, 3692.
12. (e) Arrais, A.; Dana, E.; Gervasio, G.; Gobetto, R.; Marabello, D.; Stanghellini, P. L. Eur. J. Inorg. Chem. 2004, 1505.
13. (f) Möhring, D.; Nieger, M.; Lewall, B.; Dötz, K. H. Eur. J. Org. Chem. 2005, 2620.
14. For reviews about the haptotropic migration, see: (a) Dötz, K. H. Angew. Chem., Int. Ed. Engl. 1984, 23, 587;
15. Angew. Chem. 1984, 96, 573.
16. (b) Ustynyuk, N. A. Organomet. Chem USSR 1989, 2, 20-26;
17. Metalloorg. Khim. 1989, 2, 43-53;
18. Chem. Abstr. 1989, 111, 115236.
19. (c) Semmelhack, M. F. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol.12, Chapter 9, p 979.
20. (d) Wulff, W. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol.12, pp 469-547.
21. (e) Morris, M. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Labinger, J. S., Winter, M. J., Vol.Eds.; Pergamon: Oxford, U.K., 1995; Vol.5, pp 501-504.
22. (f) Dötz, K. H.; Tomuschat, P. Chem. Soc. Rev. 1999, 28, 187.
23. (g) Oprunenko, Y. F. Russ. Chem. Rev. 2000, 69, 683-704;
24. Usp. Khim. 2000, 69, 744-746;
25. Chem. Abstr. 2000, 134, 178576.
26. (h) Dötz, K. H.; Stendel, J., Jr. In Modern Arene Chemistry; Astruc, D., Ed.; Wiley-VCH: Weinheim, Germany, 2002; pp 250-296.
27. (i) Dötz, K. H.; Jahr, H. C. Chem. Rec. 2004, 4, 61.
28. (j) Minatti, A.; Dötz, K. H. Top. Organomet. Chem. 2004, 13, 123.
29. (k) Dötz, K. H.; Wenzel, B.; Jahr, H. C. Top. Curr. Chem. 2004, 248, 63-103.
30. (a) Deubzer, B.; Fritz, H. P.; Kreiter, C. G.; Öfele, K. J. Organomet. Chem. 1967, 7, 289.
31. (b) Cunningham, S. D.; Öfele, K.; Willeford, B. J. Am. Chem. Soc. 1983, 105, 3724.
32. (c) Dötz, K. H.; Dietz, R. Chem. Ber. 1977, 110, 1555.
33. (d) Kirss, R. U., Jr.; Treichel, P. M. J. Am. Chem. Soc. 1986, 108, 853.
34. (e) Kündig, E. P.; Desobry, V.; Rivet, C.; Rudolph, B.; Splicher, S. Organometallics 1987, 6, 1173.
35. (f) Oprunenko, Y. F.; Malyugina, S. G.; Ustynyuk, Y. A.; Ustynyuk, N. A.; Kravtsov, D. N. J. Organomet. Chem. 1988, 338, 357.
36. (g) Dötz, K. H.; Stinner, C. Tetrahedron: Asymmetry 1997, 8, 1751.
37. (h) Paetsch, D.; Dötz, K. H. Tetrahedron Lett. 1999, 40, 487.
38. (i) Oprunenko, Y. F.; Malyugina, S.; Nesterenko, P.; Mityuk, D.; Malyshev, O. J. Organomet. Chem. 2000, 597, 42.
39. (j) Jahr, H. C.; Nieger, M.; Dötz, K. H. J. Organomet. Chem. 2002, 641, 185.
40. (k) Dötz, K. H.; Szesni, N.; Nieger, M.; Nättinen, K. J. Organomet. Chem 2003, 671, 58.
41. (l) Jahr, H. C.; Dötz, K. H. Chem. Rec 2004, 4, 61.
42. (m) Jahr, H. C.; Nieger, M.; Dötz, K. H. Chem Eur. J. 2005, 11, 5333.
43. (n) Dötz, K. H.; Stendel, J., Jr.; Müller, S.; Nieger, M.; Ketrat, S.; Dolg, M. Organometallics 2005, 24, 3219.
44. For reviews about manganese complexes, see: (a) Semmelhack, M. F. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol.12, Chapter 9, p 979.
45. (b) McDaniel, K. F. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol.6, pp 93-107.
46. (c) Oshima, K. Organometallic Complexes of Manganese. In Science of Synthesis; Imamoto, T., Ed.; Thieme: Stuttgart, Germany, 2002; Vol.2, p 13.
47. (d) Sweigart, D. A.; Reingold, J. A.; Son, S. U. Manganese Compounds with CO Ligands. In Comprehensive Organometallic Chemistry III; Crabtree, R. H., Mingos, D. M. P., Eds.; Elsevier Science: Oxford, U.K., 2006; Vol.5, p 761.
48. (a) King, R. B.; Efraty, A. J. Organomet. Chem. 1970, 23, 527.
49. (b) Treichel, P. M.; Johnson, J. W. Inorg. Chem. 1977, 16, 749.
50. (c) Resek, M. E.; Basolo, F. Organometallics 1984, 3, 647.
51. Ji, L.-J.; Resek, M. E.; Basolo, F. Organometallics 1984, 3, 740.
52. (d) Biagioni, R. N.; Lorkovic, I. M.; Skelton, J.; Härtung, J. B. Organometallics 1990, 9, 547.
53. Biagioni, R. N.; Luna, A. D.; Murphy, J. L. J. Organomet. Chem. 1994, 476, 183.
54. (e) Jackson, J. D.; Villa, S. J.; Bacon, D. S.; Pryke, R. D.; Carpenter, G. B. Organometallics 1994, 13, 3972.
55. (f) Sun, S.; Yeung, L. K.; Sweigart, D. A.; Lee, T.-Y.; Lee, S. S.; Chung, Y. K.; Switzer, S. R.; Pike, R. D. Organometallics 1995, 14, 2613.
56. (g) Veiros, L. F. J. Organomet. Chem. 1999, 587, 221.
57. Veiros, L. F. Organometallics 2000, 19, 3127.
58. (h) Veauthier, J. M.; Chow, A.; Fraenkel, G.; Geib, S. J.; Cooper, N. J. Organometallics 2000, 19, 261.
59. Veauthier, J. M.; Chow, A.; Fraenkel, G.; Geib, S. J.; Cooper, N. J. Organometallics 2000, 19, 3942.
60. (i) Reginato, N.; McGlinchey, M. J. Organometallics 2001, 20, 4147.
61. (j) Son, S. U.; Paik, S.-J.; Park, K. H.; Lee, Y.-A.; Lee, I. S.; Chung, Y. K.; Pike, D. A. Organometallics 2002, 21, 239.
62. (k) Decken, A.; MacKay, A. J.; Brown, M. J.; Bottomley, F. Organometallics 2002, 21, 2006.
63. (l) Rose-Munch, F.; Rose, E. Eur. J. Inorg. Chem. 2002, 1269.
64. (m) Auffrant, A.; Prim, D.; Rose-Munch, F.; Rose, E.; Schouteeten, S.; Vaissermann, J. Organometallics 2003, 22, 1898.
65. (n) Oh, M.; Reingold, J. A.; Carpenter, G. B.; Sweigart, D. A. Coord Chem. Rev. 2004, 264, 561.
66. (o) Reingold, J. A.; Virkaitis, K. L.; Carpenter, G. B.; Sun, S.; Sweigart, D. A.; Czech, P. T.; Overly, K. R. J. Am. Chem. Soc. 2005, 127, 11146.
67. (p) Snyder, C. A.; Selegue, J. P.; Tice, N. C.; Wallace, C. E.; Blankenbuehler, M. T.; Parkin, S.; Allen, K. D. E.; Beck, R. T. J. Am. Chem. Soc. 2005, 127, 15010.
68. (q) Jacques, B.; Chavarot, M.; Rose-Munch, F.; Rose, E. Inorg. Chem. 2005, 44, 5941.
69. (r) Jacques, B.; Chavarot, M.; Rose-Munch, F.; Rose, E. Angew. Chem., Int. Ed. 2006, 45, 3481.
70. (s) Pammer, F.; Sun, Y.; May, C.; Wolmershäuser, G.; Keim, H.; Krüger, H.J.; Thiel, W. R. Angew. Chem. Int. Ed. 2007, 46, 1270.
71. (t) Jacques, B.; Chanaewa, A.; Chavarot-Kerlidou, M.; Rose-Munch, F.; Rose, E.; Gérard, H. Organometallics 2008, 27, 626.
72. (u) Cetiner, D.; Tranchier, J.-P.; Rose-Munch, F.; Rose, E.; Herson, P. Organometallics 2008, 27, 784.
73. (a) Bitterwolf, T. E.; Raghuveer, K. S. Inorg. Chim. Acta 1990, 172, 59.
74. (b) Clark, G. R.; Metzler, M. R.; Whitaker, G.; Woodgate, P. D. J. Organomet. Chem. 1996, 513, 109.
75. (c) Lee, S. S.; Lee, T.-Y.; Lee, J. E.; Chung, Y. K.; Lah, M. S. Organometallics 1996, 15, 3664.
76. (d) Djukic, J.-P.; Maisse, A.; Pfeffer, M.; de Cian, A.; Fischer, J. Organometallics 1997, 16, 657.
77. Djukic, J.-P.; Maisse, A.; Pfeffer, M.; Dötz, K. H.; Nieger, M. Eur. J. Inorg. Chem. 1998, 1781.
78. (e) Tamm, M.; Bannenberg, T.; Baum, K.; Fröhlich, R.; Steiner, T.; Meyer-Friedrichsen, T.; Heck, J. Eur. J. Inorg. Chem. 2000, 1161.
79. (f) Schouteeten, S.; Tranchier, J.-P.; Rose-Munch, F.; Rose, E.; Auffrant, A.; Stephenson, G. R. Organometallics 2004, 23, 4308.
80. (g) Djukic, J.-D.; Michon, C.; Berger, A.; Pfeffer, M.; de Cian, A.; Kyritsakas-Gruber, N. J. Organomet. Chem. 2006, 691, 846.
81. (h) Dubarle Offner, J.; Schakenburg, G.; Rose-Munch, F.; Rose, E.; Dötz, K. H. Manuscript in preparation.
82. (a) Li, J.; Hunter, A. D.; McDonald, R.; Santarsiero, B. D.; Bott, S. G.; Atwood, J. L. Organometalllics 1992, 11, 3050.
83. (b) Sun, S.; Dullaghan, C. A.; Carpenter, G. B.; Rieger, A. L.; Rieger, P. H.; Sweigart, D. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 2540.
84. (c) Quian, C.; Guo, J.; Sun, J.; Chen, J.; Zheng, P. Inorg. Chem. 1997, 36, 1286.
85. (d) Prim, D.; Andrioletti, B.; Rose-Munch, F.; Rose, E.; Couty, F. Tetrahedron 2004, 60, 3325.
86. (e) Jacques, B.; Tranchier, J.-P.; Rose-Munch, F.; Rose, E.; Stephenson, G. R.; Guyard-Duhayon, C. Organometallics 2004, 23, 184.
87. (f) Bitta, J.; Fassbender, S.; Reiss, G.; Frank, W.; Ganter, C. Organometallics 2005, 24, 5176.
88. (g) Bennewitz, J.; Nieger, M.; Lewall, B.; Dötz, K. H. J. Organomet. Chem. 2005, 690, 5892.
89. (h) Packheiser, R.; Walfort, B.; Lang, H. Organometallics 2006, 25, 4579.
90. (i) Li, M.; Riache, N.; Tranchier, J.-P.; Rose-Munch, F.; Rose, E.; Herson, P.; Bossi, A.; Rigamonti, C.; Licandro, E. Synthesis 2007, 2, 277.
91. (j) Djukic, J.-P.; Hijazi, A.; Flack, H. D.; Bernardinelli, G. Chem. Soc. Rev. 2008, 37, 406.
92. (a) Fischer, E. O.; Maasböl, A. Angew. Chem. Int. Ed. Engl. 1964, 3, 580.
93. (b) Fischer, E. O. Auf dem Weg zu Carben- und Carbin-Komplexen (Nobel Lecture). Angew. Chem. 1974, 86, 651-663.
94. (a) Dötz, K. H. Angew. Chem. Int. Ed. Engl. 1975, 14, 644.
95. (b) Dötz, K. H.; Dietz, R.; Neugebauer, D. Chem. Ber. 1979, 112, 1486.
96. Bennewitz, J. Dissertation, University of Bonn, July 2007.
97. (a) Kunz, V.; Nowacki, W. Helv. Chim. Acta 1967, 50, 1052.
98. (b) van Meurs, F.; van der Toorn, J. M.; van Bekkum, H. J. Organomet. Chem. 1976, 113, 341.
99. (c) van Meurs, F.; van Koningsveld, H. J. Organomet. Chem. 1976, 118, 295.
100. (d) Boutonnet, J. C.; Le Martret, O.; Mordenti, L.; Rose, E.; Precigoux, G. J. Organomet. Chem. 1981, 221, 147.
101. (e) Boutonnet, J. C.; Levisalles, J.; Rose, E.; Precigoux, G.; Courseille, C.; Platzer, N. J. Organomet. Chem. 1983, 255, 317.
102. (f) Boutonnet, J. C.; Levisalles, J.; Rose-Munch, F.; Rose, E. J. Organomet. Chem. 1985, 290, 153.
103. (g) Boutonnet, J. C.; Rose-Munch, F.; Rose, E.; Jeannin, Y.; Robert, F. J. Organomet. Chem. 1985, 297, 185.
104. (h) Rose-Munch, F.; Rose, E.; Semra, A.; PhilocheLevisalles, M. J. Organomet. Chem. 1989, 363, 297.
105. (i) Onlsson, B.; Ullenius, C.; Jaguer, S.; Grivet, C.; Wenger, E.; Kündig, E. P. J. Organomet. Chem. 1989, 365, 243.
106. (j) Rose-Munch, F.; Aniss, K.; Rose, E.; Vaissermann, J. J. Organomet. Chem. 1991, 415, 223.
107. (k) Schmalz, H.-G.; Millies, B.; Bats, J. W.; Dürner, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 631.
108. (l) Rose-Munch, F.; Rose, E.; Djukic, J.-P.; Vaissermann, J. Eur. J. Inorg. Chem. 2000, 1295.
109. (m) Cumming, G. R.; Bernardinelli, G.; Kündig, E. P. Chem. Asian J. 2006, 1, 459.
110. Rose-Munch, F.; Rose, E.; Djukic, J.-P.; Vaissermann, J. Eur. J. Inorg. Chem. 2000, 1295.
111. (a) Hunter, A. D.; Shilliday, L.; Furey, W. S.; Zaworotko, M. J. Organometallics 1992, 11, 1550.
112. (b) Hunter, A. D.; Mozol, V.; Tsai, S. D. Organometallics 1992, 11, 2251.
113. (a) Dötz, K. H.; Stendel, J.; Nieger, M. Z. Anorg. Allg. Chem. 2009, 635, 221.
114. (b) Stendel, J., Jr. Dissertation, University of Bonn, 2004.
115. Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307-326.
116. Blessing, R. H. Acta Crystallogr. 1995, A51, 33-37.
117. (a) Blessing, R. H. J. Appl. Crystallogr. 1997, 30, A21-A26.
118. Otwinowski, Z.; Borek, D.; Majewski, W.; Minor, W. Acta Crystallogr. 2003, A59, 228-234.
119. Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473.