Synthesis and reactivity of boron-, silicon-, and tin-bridged ansa-cyclopentadienyl-cycloheptatrienyl titanium complexes (troticenophanes)

Chemistry - A European Journal

Volumn 16, Issue 38, 2010, Pages 11732-11743

  Braunschweig, Holger ^a   Fuß, Marco ^a   Mohapatra, Swagat K ^b   Kraft, Katharina ^a   Kupfer, Thomas ^a   Lang, Melanie ^a   Radacki, Krzysztof ^a   Daniliuc, Constantin G ^b   Jones, Peter G ^b   Tamm, Matthias ^b  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

Metallocenes; Oxidative addition; Sandwich complexes; Titanium; Troticenophanes

Indexed keywords

CYCLOHEPTATRIENES; CYCLOPENTADIENYLS; ELEMENTAL SULFUR; ELIMINATION REACTION; HETEROLEPTIC; METALLOCENES; MULTINUCLEAR NMR SPECTROSCOPY; ONE-POT METHOD; OXIDATIVE ADDITION PRODUCTS; OXIDATIVE ADDITIONS; REGIO-SELECTIVE; SANDWICH COMPLEXES; SEVEN-MEMBERED RINGS; SINGLE CRYSTAL X-RAY DIFFRACTION; SOLID-STATE STRUCTURES; STRUCTURAL CHARACTERIZATION; TIN ATOMS; TITANIUM COMPLEXES; TROTICENOPHANES;

ADDITION REACTIONS; BORON; BORON COMPOUNDS; DIFFRACTION; DYES; MAGNESIUM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANOMETALLICS; PLATINUM; SELENIUM; SULFUR; SYNTHESIS (CHEMICAL); TIN; TITANIUM; X RAY DIFFRACTION;

TITANIUM COMPOUNDS;

EID: 77957572871     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201001486     Document Type: Article

References (124)

1. A. G. Osborne, R. H. Whiteley, J. Organomet. Chem. 1975, 101, C27.
2. a) A. S. Abd-El-Aziz, I. Manners (Eds.), Frontiers in Transition Metal Containing Polymers; John Wiley and Sons, Inc., Hoboken, New Jersey, 2007;
3. D. E. Herbert, U. F. J. Mayer, I. Manners, Angew. Chem. 2007, 119, 5152;
4. Angew. Chem. Int. Ed. 2007, 46, 5060;
5. W. Finckh, B. Z. Tang, D. A. Foucher, D. B. Zamble, R. Ziembinski, A. Lough, I. Manners, Organometallics 1993, 12, 823;
6. V. Bellas, M. Rehahn, Angew. Chem. 2007, 119, 5174;
7. Angew. Chem. Int. Ed. 2007, 46, 5082;
8. e) C. Cui, J. Heilmann-Brohl, A. Sanchez Perucha, M. D. Thomson, H. G. Roskos, M. Wagner, F. Jaekle, Macromolecules 2010, 43, 5256;
9. M. Scheibitz, H. Li, J. Schnorr, A. Sanchez Perucha, M. Bolte, H. W. Lerner, F. Jaekle, M. Wagner, J. Am. Chem. Soc. 2009, 131, 16319;
10. J. B. Heilmann, Y. Qin, F. Jaekle, H. W. Lerner, M. Wagner, Inorg. Chim. Acta 2006, 359, 4802;
11. J. B. Heilmann, M. Scheibitz, Y. Qin, A. Sundararaman, F. Jaekle, T. Kretz, M. Bolte, H. W. Lerner, M. C. Holthausen, M. Wagner, Angew. Chem. 2006, 118, 934;
12. Angew. Chem. Int. Ed. 2006, 45, 920.
13. a) A. Berenbaum, H. Braunschweig, R. Dirk, U. Englert, J. C. Green, F. Jäkle, A. J. Lough, I. Manners, J. Am. Chem. Soc. 2000, 122, 5765;
14. J. A. Schachner, C. L. Lund, J. Wilson Quail, J. Müller, Organometallics 2005, 24, 785;
15. J. A. Schachner, C. L. Lund, J. Wilson Quail, J. Müller, Organometallics 2005, 24, 4483.
16. a) A. G. Osborne, R. H. Whiteley, R. E. Meads, J. Organomet. Chem. 1980, 193, 345;
17. D. A. Foucher, M. Edwards, R. A. Burrow, A. J. Lough, I. Manners, Organometallics 1994, 13, 4959;
18. R. Rulkens, A. J. Lough, I. Manners, Angew. Chem. 1996, 108, 1929;
19. Angew. Chem. Int. Ed. Engl. 1996, 35, 1805;
20. F. Jäkle, R. Rulkens, G. Zech, D. A. Foucher, A. J. Lough, I. Manners, Chem. Eur. J. 1998, 4, 2117.
21. a) H. Stoeckli-Evans, A. G. Osborne, R. H. Whiteley, J. Organomet. Chem. 1980, 194, 91;
22. D. Seyferth, H. P. Withers, Organometallics 1982, 1, 1275;
23. I. R. Butler, W. R. Cullen, F. W. B. Einstein, S. J. Rettig, A. J. Willis, Organometallics 1983, 2, 128.
24. a) J. K. Pudelski, D. P. Gates, R. Rulkens, A. J. Lough, I. Manners, Angew. Chem. 1995, 107, 1633;
25. Angew. Chem. Int. Ed. Engl. 1995, 34, 1506;
26. R. Rulkens, D. P. Gates, D. Balaishis, J. K. Pudelski, D. F. McIntosh, A. J. Lough, I. Manners, J. Am. Chem. Soc. 1997, 119, 10976.
27. R. Broussier, A. Da Rold, B. Gautheron, Y. Dromzee, Y. Jeannin, Inorg. Chem. 1990, 29, 1817.
28. G. R. Whittell, B. M. Partridge, O. C. Presly, C. J. Adams, I. Manners, Angew. Chem. 2008, 120, 4426;
29. Angew. Chem. Int. Ed. 2008, 47, 4354.
30. a) J. M. Nelson, A. J. Lough, I. Manners, Angew. Chem. 1994, 106, 1019;
31. Angew. Chem. Int. Ed. Engl. 1994, 33, 989;
32. U. Vogel, A. J. Lough, I. Manners, Angew. Chem. 2004, 116, 3383;
33. Angew. Chem. Int. Ed. 2004, 43, 3321.
34. a) M. J. Drewitt, S. Barlow, D. O'Hare, J. M. Nelson, P. Nguyen, I. Manners, Chem. Commun. 1996, 2153;
35. S. Fox, J. P. Dunne, M. Tacke, D. Schmitz, R. Dronskowski, Eur. J. Inorg. Chem. 2002, 3039;
36. H. Braunschweig, F. Breher, M. Kaupp, M. Gross, T. Kupfer, D. Nied, K. Radacki, S. Schinzel, Organometallics 2008, 27, 6427;
37. U. F. J. Mayer, J. B. Gilroy, D. O'Hare, I. Manners, J. Am. Chem. Soc. 2009, 131, 10382.
38. H. Braunschweig, M. Gross, K. Radacki, Organometallics 2007, 26, 6688.
39. a) H. Braunschweig, C. J. Adams, T. Kupfer, I. Manners, R. Richardson, G. R. Whittell, Angew. Chem. 2008, 120, 3886;
40. Angew. Chem. Int. Ed. 2008, 47, 3826;
41. H. Braunschweig, M. Kaupp, C. J. Adams, T. Kupfer, K. Radacki, S. Schinzel, J. Am. Chem. Soc. 2008, 130, 11376;
42. A. Berenbaum, I. Manners, Dalton Trans. 2004, 2057;
43. C. Elschenbroich, E. Schmidt, R. Gondrum, B. Metz, O. Burghaus, W. Massa, S. Wocadlo, Organometallics 1997, 16, 4589;
44. e) C. Elschenbroich, A. Bretschneider-Hurley, J. Hurley, A. Behrendt, W. Massa, S. Wocadlo, E. Reijerse, Inorg. Chem. 1995, 34, 743;
45. C. Elschenbroich, A. Bretschneider-Hurley, J. Hurley, W. Massa, S. Wocadlo, J. Pebler, Inorg. Chem. 1993, 32, 5421.
46. a) C. L. Lund, J. A. Schachner, J. Wilson Quail, J. Müller, Organometallics 2006, 25, 5817;
47. C. Elschenbroich, E. Schmidt, B. Metz, K. Harms, Organometallics 1995, 14, 4043.
48. a) H. Braunschweig, T. Kupfer, Organometallics 2007, 26, 4634;
49. H. Braunschweig, M. Homberger, C. Hu, X. Zheng, E. Gullo, G. Clentsmith, M. Lutz, Organometallics 2004, 23, 1968;
50. C. Elschenbroich, J. Hurley, B. Metz, W. Massa, G. Baum, Organometallics 1990, 9, 889;
51. K. C. Hultzsch, J. M. Nelson, A. J. Lough, I. Manners, Organometallics 1995, 14, 5496.
52. a) C. L. Lund, J. A. Schachner, J. W. Quail, J. Müller, J. Am. Chem. Soc. 2007, 129, 9313;
53. H. Braunschweig, N. Buggisch, U. Englert, M. Homberger, T. Kupfer, D. Leusser, M. Lutz, K. Radacki, J. Am. Chem. Soc. 2007, 129, 4840;
54. C. L. Lund, J. A. Schachner, I. J. Burgess, J. W. Quail, G. Schatte, J. Müller, Inorg. Chem. 2008, 47, 5992;
55. C. L. Lund, B. Bagh, J. W. Quail, J. Müller, Organometallics 2010, 29, 1977.
56. C. Elschenbroich, F. Paganelli, M. Nowotny, B. Neumilller, O. Burghaus, Z. Anorg. Allg. Chem. 2004, 630, 1599.
57. H. Braunschweig, T. Kupfer, Acc. Chem. Res. 2010, 43, 455.
58. M. Tamm, Chem. Commun. 2008, 3089.
59. M. L. H. Green, D. G. K. Ng, Chem. Rev. 1995, 95, 439.
60. a) M. Tamm, A. Kunst, T. Bannenberg, E. Herdtweck, P. Sirsch, C. J. Elsevier, J. M. Ernsting, Angew. Chem. 2004, 116, 5646;
61. Angew. Chem. Int. Ed. 2004, 43, 5530;
62. M. Tamm, A. Kunst, E. Herdtweck, Chem. Commun. 2005, 1729;
63. M. Tamm, A. Kunst, T. Bannenberg, S. Randoll, P. G. Jones, Organometallics 2007, 26, 417.
64. a) S. Büschel, A.-K. Jungton, T. Bannenberg, S. Randoll, C. G. Hrib, P. G. Jones, M. Tamm, Chem. Eur. J. 2009, 15, 2176;
65. S. Bilschel, C.-G. Daniliuc, P. G. Jones, M. Tamm, Organometallics 2010, 29, 671;
66. S. Bilschel, T. Bannenberg, C. G. Hrib, A. Glöckner, P. G. Jones, M. Tamm, J. Organomet. Chem. 2009, 694, 1244.
67. a) C. Elschenbroich, J. Plackmeyer, M. Nowotny, A. Behrendt, K. Harms, J. Pebler, O. Burghaus, Chem. Eur. J. 2005, 11, 7427;
68. C. Elschenbroich, J. Plackmeyer, M. Nowotny, K. Harms, J. Pebler, O. Burghaus, Inorg. Chem. 2005, 44, 955;
69. C. Elschenbroich, M. Wolf, J. Pebler, K. Harms, Organometallics 2004, 23, 454;
70. C. Elschenbroich, J. Plackmeyer, K. Harms, O. Burghaus, J. Pebler, Organometallics 2003, 22, 3367;
71. e) C. Elschenbroich, M. Wolf, O. Schiemann, K. Harms, O. Burghaus, J. Pebler, Organometallics 2002, 21, 5810;
72. C. Elschenbroich, F. Lu, K. Harms, Organometallics 2002, 21, 5152;
73. C. Elschenbroich, O. Schiemann, O. Burghaus, K. Harms, J. Pebler, Organometallics 1999, 18, 3273;
74. C. Elschenbroich, M. Wolf, O. Burghaus, K. Harms, J. Pebler, Eur. J. Inorg. Chem. 1999, 2173.
75. H. Braunschweig, M. Lutz, K. Radacki, A. Schaumlöffel, F. Seeler, C. Unkelbach, Organometallics 2006, 25, 4433.
76. a) H. Braunschweig, M. Lutz, K. Radacki, Angew. Chem. 2005, 117, 5792;
77. Angew. Chem. Int. Ed. 2005, 44, 5647;
78. A. Bartole-Scott, H. Braunschweig, T. Kupfer, M. Lutz, I. Manners, T. Nguyen, K. Radacki, F. Seeler, Chem. Eur. J. 2006, 12, 1266;
79. H. Braunschweig, T. Kupfer, M. Lutz, K. Radacki, J. Am. Chem. Soc. 2007, 129, 8893.
80. S. K. Mohapatra, S. Bilschel, C. Daniliuc, P. G. Jones, M. Tamm, J. Am. Chem. Soc. 2009, 131, 17014.
81. H. Braunschweig, T. Kupfer, K. Radacki, Angew. Chem. 2007, 119, 1655;
82. Angew. Chem. Int. Ed. 2007, 46, 1630.
83. P. Chadha, J. L. Dutton, M. J. Sgro, P. J. Ragogna, Organometallics 2007, 26, 6063.
84. a) B. Demerseman, P. H. Dixneuf, J. Douglade, R. Mercier, Inorg. Chem. 1982, 21, 3942;
85. H. O. Van Oven, H. J. Liefde Meijer, J. Organomet. Chem. 1970, 23, 159;
86. B. Demerseman, G. Bouquet, M. Bigorgne, J. Organomet. Chem. 1975, 101, C24.
87. G. Fraenkel, R. E. Carter, A. McLachlan, J. H. Richards, J. Am. Chem. Soc. 1960, 82, 5846.
88. a) H. Braunschweig, T. Kupfer, M. Lutz, K. Radacki, F. Seeler, R. Sigritz, Angew. Chem. 2006, 118, 8217;
89. Angew. Chem. Int. Ed. 2006, 45, 8048;
90. H. Braunschweig, T. Kupfer, J. Am. Chem. Soc. 2008, 130, 4242.
91. P. Brown, M. F. Mahon, K. C. Molloy, J. Organomet. Chem. 1992, 435, 265.
92. 2, see: S. R. Hall, C. L. Raston, B. W. Skelton, A. H. White, Inorg. Chem. 1983, 22, 4070.
93. K. A. Lyssenko, M. Y. Antipin, S. Y. Ketkov, Russ. Bull. Int. Ed. 2001, 50, 130.
94. W. Zheng, D. W. Stephan, Inorg. Chem. 1988, 27, 2386.
95. J. M. Allen, J. E. Ellis, J. Organomet. Chem. 2008, 693, 1536.
96. a) M. Herberhold, U. Steffl, W. Milius, B. Wrackmeyer, Angew. Chem. 1997, 109, 1545;
97. Angew. Chem. Int. Ed. Engl. 1997, 36, 1508;
98. M. Herberhold, U. Steffl, W. Milius, B. Wrackmeyer, Chem. Eur. J. 1998, 4, 1027;
99. M. Herberhold, U. Steffl, B. Wrackmeyer, J. Organomet. Chem. 1999, 577, 76.
100. H. Bera, H. Braunschweig, R. Doerfler, K. Hammond, A. Oechsner, K. Radacki, K. Uttinger, Chem. Eur. J. 2009, 15, 12092.
101. M. Herberhold, U. Steffl, W. Milius, B. Wrackmeyer, Angew. Chem. 1996, 108, 1927;
102. Angew. Chem. Int. Ed. Engl. 1996, 35, 1803.
103. L. Kollár, S. Gladiali, M. J. Tenorio, W. Weissensteiner, J. Cluster Sci. 1998, 9, 321.
104. M. Herberhold, U. Steffl, W. Milius, B. Wrackmeyer, J. Organomet. Chem. 1997, 533, 109.
105. J. D. Zeinstra, J. L. De Boer, J. Organomet. Chem. 1973, 54, 207.
106. a) T. Ishiyama, N. Miyaura, J. Organomet. Chem. 2000, 611, 392;
107. H. Braunschweig, C. Kollann, D. Rais, Angew. Chem. 2006, 118, 5380;
108. Angew. Chem. Int. Ed. 2006, 45, 5254;
109. A. Kerr, T. B. Marder, N. C. Norman, A. G. Orpen, M. J. Quayle, C. R. Rice, P. L. Timms, G. R. Whittell, Chem. Commun. 1998, 319;
110. W. Clegg, F. J. Lawlor, G. Lesley, T. B. Marder, N. C. Norman, A. G. Orpen, M. J. Quayle, C. R. Rice, A. J. Scott, F. E. S. Souza, J. Organomet. Chem. 1998, 550, 183;
111. C. N. Iverson, M. R. Smith III, Organometallics 1996, 15, 5155;
112. G. Lesley, P. Nguyen, N. J. Taylor, T. B. Marder, A. J. Scott, W. Clegg, N. C. Norman, Organometallics 1996, 15, 5137;
113. T. Ishiyama, N. Matsuda, M. Murata, F. Ozawa, A. Suzuki, N. Miyaura, Organometallics 1996, 15, 713;
114. C. N. Iverson, M. R. Smith III, J. Am. Chem. Soc. 1995, 117, 4403;
115. T. Ishiyama, N. Matsuda, N. Miyaura, A. Suzuki, J. Am. Chem. Soc. 1993, 115, 11018.
116. M. D. Rausch, M. Ogasa, R. D. Rogers, A. N. Rollins, Organometallics 1991, 10, 2084.
117. T. K. Panda, M. T. Gamer, P. W. Roesky, Organometallics 2003, 22, 877.
118. L. E. Manxzer, Inorg. Synth. 1982, 21, 135.
119. U. Englich, U. Hermann, I. Prass, T. Schollmeier, K. Ruhlandt-Senge, F. Ulig, J. Organomet. Chem. 2002, 646, 271.
120. W. Einholz, W. Gollinger, W. Haubold, Z. Naturforsch. 1990, B45, 25.
121. a) H. Nöth, H. Schick, W. Meister, J. Organomet. Chem. 1964, 1, 401;
122. J. T. Patton, S. G. Feng, Organometallics 2001, 20, 3399.
123. T. Yoshida, T. Matsuda, S. Otsuka, Inorg. Synth. 1990, 28, 119.
124. G. Sheldrick, Acta Crystallogr. Sect. A 2008, 64, 112.