Transition metal complexes of boron

Angewandte Chemie - International Edition

Volumn 37, Issue 13-14, 1998, Pages 1786-1801

  Braunschweig, Holger ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

B ligands; Boron; Hydroboration; Transition metal complexes

Indexed keywords

EID: 0032479754     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19980803)37:13/14<1786::aid-anie1786>3.0.co;2-c     Document Type: Review

References (150)

1. B. Post in Rare Earth Research II (Ed.: K. S. Korres) Gordon and Breach, New York, 1964, pp. 107-116.
2. R. Thompson in Progress in Boron Chemistry (Eds.: R. J. Brotherton, H. Steinberg), Pergamon, Oxford, 1970, pp. 173-230.
3. T. Lundström in Encyclopedia of Inorganic Chemistry, Vol. 1 (Ed.: R. B. King), Wiley, New York, 1994, pp. 328-338.
4. N. M. Hong, J. J. M. Franse, N. P. Thuy, J. Less-Common Met. 1989, 155, 151-159.
5. T. Tanaka, S. Otani, Y. Ishizawa, J. Less-Common Met. 1986, 177, 293-295.
6. C. E. Housecroft, T. P. Fehlner in Advances in Organometallic Chemistry, Vol. 21 (Eds.: F. G. A. Stone, R. West), 1981, Academic Press, New York, pp. 57-112.
7. C. E. Housecroft, Boranes and Metalloboranes, Wiley, New York, 1990.
8. T. P. Fehlner in Electron Deficient Boron and Carbon Clusters (Eds.: G. A. Olah, K. Wade, R. E. Williams), Wiley, New York, 1991, pp. 287-307.
9. R. N. Grimes, Chem. Rev. 1992, 92, 251-268.
10. M. F. Hawthorne, J. Organomet. Chem. 1975, 100, 97-110.
11. C. E. Housecroft in Encyclopedia of Inorganic Chemistry, Vol. 1 (Ed.: R. B. King), Wiley, New York, 1994, pp. 375-401.
12. K. Wade, Adv. Inorg. Chem. Radiochem. 1976, 18, 1-66.
13. K. Wade in Electron Deficient Boron and Carbon Clusters (Eds.: G. A. Olah, K. Wade, R. E. Williams), Wiley, New York, 1991, pp. 95-111.
14. G. E. Herberich in Comprehensive Organometallic Chemistry, Vol. 1 (Eds.: G. Wilkinson, F. G. A. Stone, E. W. Abel), Pergamon, Oxford, 1982, pp. 381-410.
15. G. E. Herberich, B. Buller, B. Hessner, W. Oschmann, J. Organomet. Chem. 1980, 195, 253-259.
16. G. E. Herberich, B. Hessner, R. Saive, J. Organomet. Chem. 1987, 319, 9-27.
17. W. Siebert, Angew. Chem. 1985, 97, 924-939; Angew. Chem. Int. Ed. Engl. 1985, 24, 943-958.
18. W. Siebert, Angew. Chem. 1985, 97, 924-939; Angew. Chem. Int. Ed. Engl. 1985, 24, 943-958.
19. A. J. Ashe III, E. Meyers, P. Shu, T. von Lehmann, J. Bastide, J. Am. Chem. Soc. 1975, 97, 6865-6866.
20. G. E. Herberich, C. Engelke, W. Pahlmann, Chem. Ber. 1979, 112, 607-624.
21. H. Werner, R. Prinz, E. Deckelmann, Chem. Ber. 1969, 102, 95-103.
22. G. Huttner, B. Krieg, Angew. Chem. 1971, 83, 541-542; Angew. Chem. Int. Ed. Engl. 1971, 10, 499-500.
23. G. Huttner, B. Krieg, Angew. Chem. 1971, 83, 541-542; Angew. Chem. Int. Ed. Engl. 1971, 10, 499-500.
24. G. Huttner, W. Gartzke, Chem. Ber. 1974, 107, 3786-3799.
25. U. Schubert, Transition Met. Chem. 1991, 16, 136-144.
26. T. D. Tilley in Chemistry of Organic Silicon Compounds, Vol. 2 (Eds.: S. Patai, Z. Rappoport), Wiley, New York, 1989, pp. 1415-1477.
27. C. Zybill, H. Handwerker, H. Friedrich in Advances in Organometallic Chemistry, Vol. 36 (Eds.: F. G. A. Stone, R. West), 1994, Academic Press, New York, pp. 229-281.
28. P. D. Lickiss, Chem. Soc. Rev. 1992, 21, 271-279.
29. G. Schmid, Angew. Chem. 1970, 82, 920-930; Angew. Chem. Int. Ed. Engl. 1970, 9, 819-828.
30. G. Schmid, Angew. Chem. 1970, 82, 920-930; Angew. Chem. Int. Ed. Engl. 1970, 9, 819-828.
31. D. F. Shriver, J. Am. Chem. Soc. 1963, 85, 3509-3510.
32. M. P. Johnson, D. F. Shriver, J. Am. Chem. Soc. 1966, 88, 301-304.
33. H. Braunschweig, T. Wagner, Chem. Ber. 1994, 127, 1613-1614.
34. H. Braunschweig, T. Wagner, Z. Naturforsch. B 1996, 51, 1618-1620.
35. H. Braunschweig, unpublished results.
36. J. M. Burlitch, J. H. Burk, M. E. Leonowicz, R. E. Hughes, Inorg. Chem. 1979, 18, 1702-1709.
37. There are no spectroscopic data that would indicate a comparable migration from the metal to the cyclopentadienyl ligands in the case of 2, even at lower temperatures; see ref. [30].
38. G. W. Parshall, J. Am. Chem. Soc. 1964, 86, 361-364.
39. P. Powell, H. Nöth, J. Chem. Soc. Chem. Commun. 1966, 637-638.
40. J. Grobe, R. Martin, Z. Anorg. Allg. Chem. 1992, 607, 146-152.
41. 2Ti unit to which two neutral boranes are coordinated: J. F. Hartwig, C. N. Muhoro, X. He, J. Am. Chem. Soc. 1996, 118, 10936-10937.
42. J. F. Hartwig, S. R. De Gala, J. Am. Chem. Soc. 1994, 116, 3661-3662.
43. D. R. Lantero, D. H. Motry, D. L. Ward, M. R. Smith III, J. Am. Chem. Soc. 1994, 116, 10811-10812.
44. J. F. Hartwig, X. He, Organometallics 1996, 15, 5350-5358.
45. J. F. Hartwig, X. He, Angew. Chem. 1996, 108, 352-354; Angew. Chem. Int. Ed. Engl. 1996, 35, 315-317.
46. J. F. Hartwig, X. He, Angew. Chem. 1996, 108, 352-354; Angew. Chem. Int. Ed. Engl. 1996, 35, 315-317.
47. D. H. Berry, Q. Jiang, J. Am. Chem. Soc. 1987, 109, 6210-6212.
48. K. M. Waltz, X. He, C. Muhoro, J. F. Hartwig, J. Am. Chem. Soc. 1995, 117, 11357-11358.
49. X. He, J. F. Hartwig, Organometallics 1996, 15, 400-407.
50. J. F. Hartwig, S. Huber, J. Am. Chem. Soc. 1993, 115, 4908-4909.
51. C. Dai, G. Stringer, J. F. Corrigan, N. J. Taylor, T. B. Marder, N. C. Norman, J. Organomet. Chem. 1996, 513, 273-275.
52. C. Dai, G. Stringer, T. B. Marder, A. J. Scott, W. Clegg, N. C. Norman, Inorg. Chem. 1997 36, 272-273.
53. S. A. Westcott, N. J. Taylor, T. B. Marder, R. T. Baker, N. J. Jones, J. C. Calabrese, J. Chem. Soc. Chem. Commun. 1991, 304-305.
54. R. T. Baker, J. C. Calabrese, S. A. Westcott, P. Nguyen, T. B. Marder, J. Am. Chem. Soc. 1993, 115, 4367-4368.
55. C. Einertshofer, Dissertation, Ludwig-Maximilians-Universität, München, 1992.
56. C. N. Iverson, M. R. Smith III, J. Am. Chem. Soc. 1995, 117, 4403-4404.
57. G. Lesley, P. Nguyen, N. J. Taylor, T. B. Marder, A. J. Scott, W. Clegg, N. C. Norman, Organometallics 1996, 15, 5137-5154.
58. J. R. Knorr, J. S. Merola, Organometallics 1990, 9, 3008-3010.
59. P. Nguyen, H. P. Blom, S. A. Westcott, N. J. Taylor, T. B. Marder, J. Am. Chem. Soc. 1993, 115, 9329-9330.
60. [57]
61. H. Wadepohl, U. Arnold, H. Pritzkow, Angew. Chem. 1997, 109, 1009-1011; Angew. Chem. Int. Ed. Engl. 1997, 36, 974-976.
62. H. Wadepohl, U. Arnold, H. Pritzkow, Angew. Chem. 1997, 109, 1009-1011; Angew. Chem. Int. Ed. Engl. 1997, 36, 974-976.
63. R. T. Baker, D. W. Ovenall, J. C. Calabrese, S. A. Westcott, N. J. Taylor, I. D. Willams, T. B. Marder, J. Am. Chem. Soc. 1990. 112, 9399-9400.
64. T. Ishiyama, N. Matsuda, M. Murata, F. Ozawa, A. Suzuki, N. Miyaura, Organometallics 1996, 15, 713-720.
65. C. N. Iverson, M. R. Smith III, Organometallics 1996, 15, 5155-5165.
66. S. Onozawa, Y. Hatanaka, T. Sakakura, S. Shimada, M. Tanaka, Organometallics 1996, 15, 5450-5452.
67. H. Braunschweig, B. Ganter, M. Koster, T. Wagner, Chem. Ber. 1996, 129, 1099-1101.
68. H. Braunschweig, C. Kollann, M. Müller, Eur. J. Inorg. Chem. 1998, 291-293.
69. J. D. Basil, A. A. Aradi, N. K. Bhattacharyya, N. P. Rath, C. Eigenbrot, T. P. Fehlner, Inorg. Chem. 1990, 29, 1260-1270.
70. D. J. Elliot, C. J. Levy, R. J. Puddephatt, D. G. Holah, A. N. Hughes, V. R. Magnuson, I. M. Moser, Inorg. Chem. 1990, 29, 5014-5015.
71. 3)}], see Y. Kawano, M. Shimoi in Advances in Boron Chemistry (Ed.: W. Siebert), The Royal Society of Chemistry, Cambridge, 1997, pp. 393-396.
72. H. C. Brown, B. C. Subba Rao, J. Am. Chem. Soc. 1956, 78, 2582-2588.
73. G. Urry, J. Kerrigan, T. D. Parsons, H. I. Schlesinger, J. Am. Chem. Soc. 1954, 76, 5299-5301.
74. P. Ceron, A. Finch, J. Frey, G. Urry, J. Kerrigan, T. D. Parsons, H. I. Schlesinger, J. Am. Chem. Soc. 1959, 81, 6368-6371.
75. K. Burgess, W. A. van der Donk, S. A. Westcott, T. B. Marder, R. T. Baker, J. C. Calabrese, J. Am. Chem. Soc. 1992, 114, 9350-9359.
76. 3RhCl] with CatBH can be found in ref. [70].
77. 3RhCl] with CatBH can be found in ref. [70].
78. 3RhCl] with CatBH can be found in ref. [70].
79. S. Camanyes, F. Maseras, M. Moreno, A. Lledós, J. M. Lluch, J. Bertrán, Angew. Chem. 1997, 109, 259-261; Angew. Chem. Int. Ed. Engl. 1997, 26, 265-266.
80. S. Camanyes, F. Maseras, M. Moreno, A. Lledós, J. M. Lluch, J. Bertrán, Angew. Chem. 1997, 109, 259-261; Angew. Chem. Int. Ed. Engl. 1997, 26, 265-266.
81. S. G. Feng, P. S. White, J. L. Templeton, J. Am. Chem. Soc. 1990, 112, 8192-8193.
82. S. G. Feng, P. S. White, J. L. Templeton, J. Am. Chem. Soc. 1992, 114, 2951-2960.
83. K. M. Harmon, F. E. Cummings, J. Am. Chem. Soc. 1962, 84, 1751.
84. H. Nöth, G. Schmid. Angew. Chem. 1963, 75, 861-862; Angew. Chem. Int. Ed. Engl. 1963, 2, 623-624.
85. H. Nöth, G. Schmid. Angew. Chem. 1963, 75, 861-862; Angew. Chem. Int. Ed. Engl. 1963, 2, 623-624.
86. H. Nöth, B. Wrackmeyer in NMR Basic Principles and Progress, Vol. 14 (Eds.: P. Diehl, E. Fluck, R. Kosfeld), Springer, New York, 1989, pp. 271-272.
87. J. W. Lauher, R. H. Hoffmann, J. Am. Chem. Soc. 1976, 98, 1729-1742.
88. M. R. Churchill, F. J. Hollander, R. R. Schrock, J. Am. Chem. Soc. 1978, 100, 647-648.
89. R. R. Schrock, Acc. Chem. Res. 1979, 12, 98-104.
90. G.-H. Lee, S.-M. Peng, G.-M. Yang, S.-F. Lush, R.-S. Liu, Organometallics 1989, 8, 1106-1111.
91. E. Lindner, M. Pabel, R. Fawzi, H. A. Mayer, K. Wurst, J. Organomet. Chem. 1992, 435, 109-121.
92. R. D. Closson, J. Kozikowski, T. H. Coffield, J. Org. Chem. 1957, 22, 598.
93. R. A. Fischer, M. M. Schulte, T. Priermeier, J. Organomet. Chem. 1995, 493, 139-142.
94. 3] is coordinated by four amino groups and is thus electronically saturated.
95. B. E. R. Schilling, R. Hoffmann, D. L. Lichtenberger, J. Am. Chem. Soc. 1979, 101, 585-591.
96. P. Eilbracht, P. Dahler, Chem. Ber. 1980, 113, 542-554.
97. T. Debaerdemaeker, K. Berhalter, C. Weisemann, H. A. Brune, Acta Crystallogr. Sect. C 1987, 43, 1253-1255.
98. R. K. Harris, I. J. McNaught, P. Reams, K. J. Packer, Magn. Reson. Chem. 1991, 29, 60-72.
99. M. R. Churchill, J. J. Hackbarth, Inorg. Chem. 1975, 14, 2047-2051.
100. R. Hoffmann, A. R. Rossi, Inorg. Chem. 1975, 14, 365-374.
101. K. M. Melmed, D. Coucouvanis, S. J. Lippard, Inorg. Chem. 1973, 12, 232-236.
102. W. K. Kot, N. M. Edelstein, A. Zalkin, Inorg. Chem. 1987, 26, 1339-1341.
103. M. F. Lappert, A. Singh, J. L. Atwood, W. E. Hunter, J. Chem. Soc. Chem. Commun. 1983, 206-207.
104. P. R. Rablen, J. F. Hartwig, S. P. Nolan, J. Am. Chem. Soc. 1994, 116, 4121-4122.
105. S. Sakaki, T. Kikuno, Inorg. Chem. 1997, 36, 226-229.
106. H. Braunschweig, T. Wagner, Angew. Chem. 1995, 107, 904-905; Angew. Chem. Int. Ed. Engl. 1995, 34, 825-826.
107. H. Braunschweig, T. Wagner, Angew. Chem. 1995, 107, 904-905; Angew. Chem. Int. Ed. Engl. 1995, 34, 825-826.
108. H. Braunschweig, B. Ganter, J. Organomet. Chem. 1997, 545, 163-167.
109. H. Braunschweig, U. Englert, C. Kollann, Eur. J. Inorg. Chem. 1998, 465-468.
110. H. Nöth, personal communication.
111. K. Folting, J. C. Huffman, L. N. Lewis, K. G. Caulton, Inorg. Chem. 1979, 18, 3483-3486.
112. M. Akita, S. Kato, M. Terada, Y. Masaki, M. Tanaka, Y. Moro-oka, Organometallics 1997, 16, 2392-2412.
113. H. Braunschweig, M. Müller, Chem. Ber. 1997, 130, 1295-1298.
114. H. C. Brown, Hydroboration, Wiley, New York, 1962.
115. H. C. Brown, G. W. Kramer, A. B. Levy, M. M. Midland, Organic Syntheses via Boranes, Wiley, New York, 1975.
116. H. C. Brown, A. Pelter, K. Smith, Borane Reagents, Academic Press, New York, 1988.
117. C. S. Cundy, B. M. Kingston, M. F. Lappert, Adv. Organomet. Chem. 1973, 11, 297-330.
118. J. L. Speier, Adv. Organomet. Chem. 1979, 17, 407-447.
119. J. P. Collman, L. S. Hegedus, J. R. Norton, R. G. Finke, Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley, CA, 1987.
120. D. Männig, H. Nöth, Angew. Chem. 1985, 97, 854-855; Angew. Chem. Int. Ed. Engl. 1985, 24, 878-879.
121. D. Männig, H. Nöth, Angew. Chem. 1985, 97, 854-855; Angew. Chem. Int. Ed. Engl. 1985, 24, 878-879.
122. K. Burgess, M. J. Ohlmeyer, Chem. Rev. 1991, 91, 1179-1191.
123. J. D. Hewes, C. W. Kreimendahl, T. B. Marder, M. F. Hawthorne, J. Am. Chem. Soc. 1984, 106, 5757-5759.
124. A. E. Dorigo, P. von R. Schleyer, Angew. Chem. 1995, 107, 108-110; Angew. Chem. Int. Ed. Engl. 1995, 34, 115-117.
125. A. E. Dorigo, P. von R. Schleyer, Angew. Chem. 1995, 107, 108-110; Angew. Chem. Int. Ed. Engl. 1995, 34, 115-117.
126. D. A. Evans, G. C. Fu, B. A. Anderson, J. Am. Chem. Soc. 1992, 114, 6679-6685.
127. S. A. Westcott, H. P. Blom, T. B. Marder, R. T. Baker, J. C. Calabrese, Inorg. Chem. 1993, 32, 2175-2182.
128. D. G. Musaev, A. M. Mebel, K. Morokuma, J. Am. Chem. Soc. 1994, 116, 10693-10702.
129. K. Burgess, M. J. Ohlmeyer, J. Org. Chem. 1988, 53, 5178-5179.
130. D. A. Evans, G. C. Fu, A. H. Hoveyda, J. Am. Chem. Soc. 1988, 110, 6917-6918.
131. T. Hayashi, Y. Matsumoto, Y. Ito, J. Am. Chem. Soc. 1989, 111, 3426-3428.
132. K. Burgess, J. Cassidy, M. J. Ohlmeyer, J. Org. Chem. 1991, 56, 1020-1027.
133. M. Sato, Y. Nomoto, N. Miyaura, A. Suzuki, Tetrahedron Lett. 1989, 30, 3789-3792.
134. I. D. Gridnev, N. Miyaura, A. Suzuki, Organometallics 1993, 12, 589-592.
135. K. N. Harrison, T. J. Marks, J. Am. Chem. Soc. 1992, 114, 9220-9221.
136. D. H. Motry, M. R. Smith III, J. Am. Chem. Soc. 1995, 117, 6615-6616.
137. X. He, J. F. Hartwig, J. Am. Chem. Soc. 1996, 118, 1696-1702.
138. D. H. Motry, A. G. Brazil, M. R. Smith III, J. Am. Chem. Soc. 1997, 119, 2743-2744.
139. S. Pereira, M. Srebnik, Organometallics 1995, 14, 3127-3128.
140. S. Pereira, M. Srebnik, J. Am. Chem. Soc. 1996, 118, 909-910.
141. R. T. Baker, J. C. Calabrese, S. A. Westcott, J. Organomet. Chem. 1995, 498, 109-117.
142. T. Ishiyama, M. Yamamoto, N. Miyaura, Chem. Commun. 1997, 689-690.
143. R. T. Baker, P. Nguyen, T. B. Marder, S. A. Westcott, Angew. Chem. 1995, 107, 1451-1452; Angew. Chem. Int. Ed. Engl. 1995, 34, 1336-1337.
144. R. T. Baker, P. Nguyen, T. B. Marder, S. A. Westcott, Angew. Chem. 1995, 107, 1451-1452; Angew. Chem. Int. Ed. Engl. 1995, 34, 1336-1337.
145. M. Suginome, H. Nakamura, Y. Ito, Chem. Commun. 1996, 2777-2778.
146. T. Ishiyama, K. Nishijima, N. Miyaura, A. Suzuki, J. Am. Chem. Soc. 1993, 115, 7219-7225.
147. T. B. Marder, N. C. Norman, C. R. Rice, E. G. Robins, Chem. Commun. 1997, 53-54.
148. R. H. Crabtree, Chem. Rev. 1985, 245-269.
149. J. A. Maguire, A. S. Goldman, J. Am. Chem. Soc. 1991, 113, 6706-6708.
150. J. F. Hartwig, K. M. Waltz, Science 1997, 277, 211-213.