Synthesis and reactivity studies of iminoboryl complexes

Journal of the American Chemical Society

Volumn 130, Issue 25, 2008, Pages 7974-7983

  Braunschweig, Holger ^a   Kupfer, Thomas ^a   Radacki, Krzysztof ^a   Schneider, Achim ^a   Seeler, Fabian ^a   Uttinger, Katharina ^a   Wu, Hongmei ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

REACTIVITY (CHEMICAL); SYNTHESIS (OF CHIRAL IONIC LIQUIDS);

COMPLEXATION;

ALKYNYL GROUP; BORANE DERIVATIVE; IMINOBORANE; IMINOBORYL COMPLEX; RHODIUM; TRANSITION ELEMENT;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; COMPLEX FORMATION; CRYSTAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLIGOMERIZATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 45749095462     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8016889     Document Type: Article

References (110)

1. For an overview on transition metal σ-alkynyl complexes see: (a) Lewis, J.; Khan, M. S.; Kakkar, A. K.; Johnson, B. F. G.; Marder, T. B.; Fyfe, H. B.; Wittmann, F.; Friend, R. H.; Dray, A. E. J. Organomet. Chem. 1992, 425, 165-176.
2. (b) Khan, M. S.; Kakkar, A. K.; Long, N. J.; Lewis, J.; Raithby, P.; Nguyen, P.; Marder, T. B.; Wittmann, F.; Friend, R. H. J. Mater. Chem. 1994, 4, 1227-1232.
3. (c) Long, N. J. Angew. Chem. 1995, 107, 3756;.
4. Angew. Chem. Int. Ed. Engl. 1995, 34, 21-38.
5. (d) Whittall, I. R.; McDonagh, A. M.; Humphrey, M. G.; Samoc, M. Adv. Organomet. Chem. 1998, 42, 291-362.
6. (e) Whittall, I. R.; McDonagh, A. M.; Humphrey, M. G.; Samoc, M. Adv. Organomet. Chem. 1999, 43, 349-405.
7. (f) Manners, I. Synthetic Metal-Containing Polymers; Wiley-VCH: Weinheim, Germany, 2002; 153-179.
8. (g) Long, N. J.; Williams, C. K. Angew. Chem. 2003, 115, 26902722;.
9. Angew. Chem., Int. Ed. 2003, 42, 2586-2617.
10. (h) Powell, C. E.; Humphrey, M. G. Coord. Chem. Rev. 2004, 248, 725-756.
11. (i) Cifuentes, M. P.; Humphrey, M. G. J. Organomet. Chem. 2004, 689, 3968-3981.
12. (j) Wong, W. Y.; Ho, C. L. Coord. Chem. Rev. 2006, 250, 2627-2690.
13. (k) Wong, W.-Y. J. Chem. Soc., Dalton Trans. 2007, 4495-4510.
14. (l) Morrall, J. P.; Dalton, G. T.; Humphrey, M. G.; Samoc, M. Adv. Organomet. Chem. 2008, 55, 61-136, and references therein.
15. (a) Takahashi, S.; Takai, Y.; Morimoto, H.; Sonogashira, K.; Hagihara, N. Mol. Cryst. Liq. Cryst. 1982, 82, 139-143.
16. (b) Takahashi, S.; Takai, Y.; Morimoto, H.; Sonogashira, K. J. Chem. Soc., Chem. Commun. 1984, 3, 5.
17. (a) Younus, M.; Köhler, A.; Cron, S.; Chawdhury, N.; Al-Mandhary, M. R. A.; Khan, M. S.; Lewis, J.; Long, N. J.; Friend, R. H.; Raithby, P. R. Angew: Chem. 1998, 110, 3180-3183;
18. Angew. Chem. Int. Ed. 1998, 37, 3036-3039.
19. (b) Wong, W.-Y.; Wong, W.-K.; Raithby, P. R. J. Chem. Soc., Dalton Trans. 1998, 2761-2766.
20. (c) Ferri, A.; Polzonetti, G.; Licoccia, S.; Paolesse, R.; Favretto, D.; Traldi, P.; Russo, M. V. J. Chem. Soc., Dalton Trans. 1998, 4063-4070.
21. (d) Wong, W.-Y.; Choi, K.-H.; Lu, G.-L.; Shi, J.-X. Macromol. Rapid Commun. 2001, 22, 461-465.
22. (a) Côté, M.; Haynes, P. D.; Molteni, C. Phys. Rev. B: Condens. Matter 2001, 63, 125207.
23. (b) Marder, T. B. Angew. Chem. 2008, 120, 248-250;
24. Angew. Chem. Int. Ed. 2008, 47: 242-244.
25. (a) Nöth, H. Angew. Chem. 1988, 100, 1664-1684;
26. Angew. Chem., Int. Ed. Engl. 1988, 27, 1603-1623.
27. (b) Braun, U.; Bock, B.; Nöth, H.; Schwab, I.; Schwartz, M.; Weber, S.; Wietelmann, U. Eur. J. Inorg. Chem. 2004, 3612-3628, and references therein.
28. Paetzold, P. Adv. Inorg. Chem. 1987, 31, 123-170.
29. (a) Baird, N. C.; Datta, R. K. Inorg. Chem. 1972, 11, 17-19.
30. (b) Armstrong, D. R.; Clark, D. T. Theor. Chim. Acta 1972, 24, 307-316.
31. (a) Irvine, G. J.; Lesley, M. J. G.; Marder, T. B.; Norman, N. C.; Rice, C. R.; Robins, E. G.; Roper, W. R.; Whittell, G. R.; Wright, L. J. Chem. Rev. 1998, 98, 2685-2722.
32. (b) Braunschweig, H. Angew. Chem. 1998, 110, 18821898;.
33. Angew. Chem. Int. Ed. 1998, 17, 1786-1801.
34. (c) Braunschweig, H.; Colling, M. Coord. Chem. Rev. 2001, 223, 1-51.
35. (d) Aldridge, S.; Coombs, D. L. Coord. Chem. Rev. 2004, 248, 535-559.
36. (e) Braunschweig, H.; Kollann, C.; Rais, D. Angew. Chem. 2006, 118, 53805400;.
37. Angew. Chem. Int. Ed. 2006, 45, 5254-5274 and references therein.
38. Braunschweig, H.; Radacki, K.; Rais, D.; Uttinger, K. Angew. Chem. 2006, 118, 169172;.
39. Angew. Chem. Int. Ed. 2006, 45, 162-165.
40. (a) Clegg, W. F.; Lawlor, J.; Lesley, G.; Marder, T. B.; Norman, N.; Orpen, A. G.; Quayle, M. J.; Rice, C. R.; Scott, A. J.; Souza, F. E. S. J. Organomet. Chem. 1998, 550, 183-192.
41. (b) Braunschweig, H.; Radacki, K.; Rais, D.; Seeler, F. Organometallics 2004, 23, 5545-5549.
42. (c) Braunschweig, H.; Radacki, K.; Rais, D.; Whittell, G. R. Angew. Chem. 2005, 117, 1217-1219;
43. Angew. Chem. Int. Ed. 2005, 44, 1192-1194.
44. (d) Braunschweig, H.; Radacki, K.; Rais, D.; Seeler, F.; Uttinger, K. J. Am. Chem. Soc. 2005, 127, 1386-1387.
45. (e) Braunschweig, H.; Whittell, G. R. Chem. Eur. J. 2005, 11, 6128-6133.
46. (f) Braunschweig, H.; Radacki, K.; Rais, D.; Scheschkewitz, D. Angew. Chem. 2005, 117, 57965799;.
47. Angew. Chem. Int. Ed. 2005, 44, 5651-5654.
48. (g) Braunschweig, H.; Radacki, K.; Rais, D.; Seeler, F. Angew. Chem. 2006, 118, 1087-1090;
49. Angew. Chem. Int. Ed. 2006, 45, 1066-1069.
50. (h) Braunschweig, H.; Radacki, K.; Uttinger, K. Angew. Chem. 2007, 119, 40544057;.
51. Angew. Chem. Int. Ed. 2007, 46, 3979-3982.
52. (i) Braunschweig, H.; Brenner, P.; Müller, A.; Radacki, K.; Rais, D.; Uttinger, K. Chem. Eur. J. 2007, 13, 7171-7176.
53. (j) Braunschweig, H.; Leech, R.; Rais, D.; Radacki, K.; Uttinger, K. Organometallics 2008, 27, 418-422.
54. (k) Braunschweig, H.; Gruss, K.; Radacki, K.; Uttinger, K. Eur. J. Inorg. Chem. 2008, 1462-1466.
55. Braunschweig, H.; Radacki, K.; Rais, D.; Schneider, A.; Seeler, F. J. Am. Chem. Soc. 2007, 129, 10350-10351.
56. (a) Mann, B. E.; Musco, A. J. Chem. Soc, Dalton Trans. 1980, 776-785.
57. (b) Haase, M.; Klingebiel, U.; Boese, R.; Polk, M. Chem. Ber. 1986, 119, 1117-1126.
58. Zhu, J.; Lin, Z.; Marder, T. B. Inorg. Chem. 2005, 44, 9384-9390.
59. (a) Burgess, K.; Van der Donk, W. A.; Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. J. Am. Chem. Soc. 1992, 114, 9350-9359.
60. (b) Dai, C.; Stringer, G.; Marder, T. B.; Scott, A. J.; Clegg, W.; Norman, N. C. Inorg. Chem. 1997, 36, 272-273.
61. (c) Souza, F. E. S.; Nguyen, P.; Marder, T. B.; Scott, A. J.; Clegg, W. Inorg. Chim. Acta 2005, 358, 1501-1509.
62. (a) Marder, T. B.; Zargarian, D.; Calabrese, J. C.; Herskovitz, T.; Milstein, D. J. Chem. Soc, Chem. Commun. 1987, 1484-1485.
63. (b) Zargarian, D.; Chow, P.; Taylor, N. J.; Marder, T. B. J. Chem. Soc., Chem. Commun. 1989, 540-544.
64. (c) Chow, P.; Zargarian, D.; Taylor, N. J.; Marder, T. B. J. Chem. Soc., Chem. Commun. 1989, 1545-1547.
65. (d) Davies, S. J.; Johnson, B. F. G.; Khan, M. S.; Lewis, J. J. Chem. Soc., Chem. Commun. 1991, 187-188.
66. (e) Fyfe, H. B.; Mlekuz, M.; Zargarian, D.; Taylor, N. J.; Marder, T. B. J. Chem. Soc., Chem. Commun. 1991, 188-190.
67. (f) Khan, M. S.; Davies, S. J.; Kakkar, A. K.; Schwartz, D.; Lin, B.; Johnson, B. F. G.; Lewis, J. J. Organomet. Chem. 1992, 424, 87-97.
68. (g) Rourke, J. P.; Bruce, D. W.; Marder, T. B. J. Chem. Soc, Dalton Trans. 1995, 317-318.
69. (h) Rourke, J. P.; Batsanov, A. S.; Howard, J. A. K.; Marder, T. B. J. Chem. Soc., Chem. Commun. 2001, 2626-2627.
70. (i) Rourke, J. P.; Stringer, G.; Chow, P.; Deeth, R. J.; Yufit, D. S.; Howard, J. A. K.; Marder, T. B. Organometallics, 2002, 21, 429-437.
71. (j) Zhu, X.; Ward, R. M.; Albesa-Jové, D.; Howard, J. A. K.; Porrès, L.; Beeby, A.; Low, P. J.; Wong, W.-K.; Marder, T. B. Inorg. Chim. Acta 2006, 359, 2859-2863.
72. Haubold, W.; Kraatz, U. Z. Anorg. Allg. Chem. 1976, 421, 105-110.
73. (a) Paetzold, P. Phosphorus, Sulfur Silicon Relat. Elem. 1994, 93-94, 39-50.
74. (b) Münster, J.; Paetzold, P.; Schröder, E.; Schwan, H.; Bennigsen-Mackiewicz, T. Z. Anorg. Allg. Chem. 2004, 630, 2641-2651.
75. (a) Delpy, K.; Schmitz, D.; Paetzold, P. Chem. Ber. 1983, 116, 2994-2999.
76. (b) Paetzold, P.; Delpy, K.; Boese, R. Z. Naturforsch. B 1988, 43, 839-845.
77. (a) Männig, D.; Nöth, H.; Schwartz, M.; Weber, S.; Wietelmann, U. Angew. Chem. 1985, 97, 979-980;
78. Angew. Chem. Int. Ed. Engl. 1985, 24, 998-999.
79. (b) Paetzold, P.; Delpy, K. Chem. Ber. 1985, 118, 2552-2553.
80. (c) Bulak, E.; Herberich, G. E.; Manners, I.; Mayer, H.; Paetzold, P. Angew. Chem. 1988, 100, 964965;.
81. Angew. Chem. Int. Ed. Engl. 1988, 27, 958-959.
82. (d) Bulak, E.; Paetzold, P. Z. Anorg. Allg. Chem. 2000, 626, 1277-1278.
83. (a) Nöth, H.; Weber, S. Chem. Ber. 1985, 118, 2554-2556.
84. (b) Böck, B.; Braun, U.; Habereder, T.; Mayer, P.; Nöth, H. Z. Naturforsch. B 2004, 59, 681-684.
85. (a) Paetzold, P.; Delpy, K.; Hughes, R. P.; Herrmann, W. A. Chem. Ber. 1985, 118, 1724-1725.
86. (b) Paetzold, P.; Hahnfeld, D.; Englert, U.; Wojnowski, W.; Dreczewski, B.; Pawelec, Z.; Walz, L. Chem. Ber. 1992, 125, 1073-1078.
87. (a) Paetzold, P.; von Plotho, C.; Schwan, H.; Meier, H. U. Z. Naturforsch. B 1984, 39, 610-614.
88. (b) Nöth, H.; Weber, S. Chem. Ber. 1985, 118, 2144-2146.
89. (c) Brandl, A.; Nöth, H. Chem. Ber. 1985, 118, 3759-3770.
90. (a) Braunschweig, H.; Müller, M. Chem. Ber. 1997, 130, 1295-1298.
91. (b) Irvine, G. J.; Rickard, C. E. F.; Roper, W. R.; Williamson, A.; Wright, L. J. Angew. Chem. 2000, 112, 978980;.
92. Angew. Chem., Int. Ed. 2000, 39, 948-950.
93. (c) Rickard, C. E. F.; Roper, W. R.; Williamson, A.; Wright, L. J. Organometallics 2002, 21, 4862-4872.
94. (d) Clark, G. R.; Irvine, G. J.; Roper, W. R.; Wright, L. J. J. Organomet. Chem. 2003, 680, 81-88.
95. (a) Cui, Q.; Musaev, D. G.; Morokuma, K. Organometallics 1998, 17, 742-751.
96. (b) Sakaki, S.; Kai, S.; Sugimoto, M. Organometallics 1999, 18, 4825-4837.
97. (a) Ha, T. B. T.; Souchard, J. P.; Wimmer, F. L.; Johnson, N. P. Polyhedron 1990, 9, 2647-2649.
98. (b) Jaska, C. A.; Temple, K.; Lough, A. J.; Manners, I. J. Am. Chem. Soc. 2003, 125, 9424-9434.
99. It should be noted that electrophilic attack at the beta carbon of metal acetylides is well known (analogous to the attack by electrophiles at the nitrogen atom of the iminoboryls) as discussed in detail in the following: Kostnic, N. M.; Fenske, R. F. Organometallics 1982, 1, 974-982.
100. Kroner, J.; Nöth, H.; Polborn, K.; Stolpmann, H.; Tacke, M.; Thomann, M. Chem. Ber 1993, 126., 1995-2002.
101. Aldridge, S.; Calder, R. J.; Rossin, A.; Dickinson, A. A.; Willock, D. J.; Jones, C.; Evans, D. J.; Steed, J. W.; Light, M. E.; Coles, S. J.; Hursthouse, M. B. J. Chem. Soc., Dalton Trans. 2002, 2020-2026.
102. Paetzold, P.; Pelzer, C.; Boese, R. Chem. Ber. 1988, 121, 51-59.
103. For unsymmetric platinum bis(acetylides) see: Nguyen, P.; Lesley, G.; Marder, T. B.; Ledoux, I.; Zyss, J. Chem. Mater. 1997, 9, 406-408.
104. Iverson, C. N.; Smith, M. R. J. Am. Chem. Soc. 1995, 117, 4403-4404.
105. Yoshida, T.; Matsuda, T.; Otsuka, S. Inorg. Synth. 1979, 19, 107-110.
106. Yoshida, T.; Otsuka, S. Inorg. Synth. 1979, 19, 101-107.
107. Price, R. T.; Andersen, R. A.; Muetterties, E. L. J. Organomet. Chem. 1989, 376, 407-417.
108. 2.
109. Teuben, J. H.; Liefde Meijer, H. J. J. Organomet. Chem. 1969, 17, 87-93.
110. Sheldrick, G. Acta Crystallogr. 2008, A64, 112-122.