Trans influence of boryl ligands and comparison with C, Si, and Sn ligands

Inorganic Chemistry

Volumn 44, Issue 25, 2005, Pages 9384-9390

  Zhu, Jun ^a   Lin, Zhenyang ^a   Marder, Todd B ^b  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

^b DURHAM UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BORON; CARBON; LIGAND; ORGANOMETALLIC COMPOUND; SILICON; TIN;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY;

BORON; CARBON; LIGANDS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; SILICON; TIN;

EID: 29544438170     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic0513641     Document Type: Article

References (95)

1. For recent reviews, see: (a) Hartwig, J. F.; Waltz, K. M.; Muhoro, C. N.; He, X.; Eisenstein, O.; Bosque, R.; Maseras, F. In Advances of Boron Chemistry, Siebert, W., Ed.; Special Publication No. 201; The Royal Society of Chemistry: Cambridge, U.K., 1997; p 373.
2. (b) Wadepohl, H. Angew. Chem., Int. Ed. Engl. 1997, 36, 2441.
3. (c) 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.
4. (d) Braunschweig, H. Angew. Chem., Int. Ed. 1998, 37, 1786.
5. (e) Smith, M. R., III. Prog. Inorg. Chem. 1999, 48, 505.
6. (f) Braunschweig, H.; Colling, M. Coord. Chem. Rev. 2001, 223, 1.
7. For a recent structural and computational study, see: (g) Lam, W. H.; Shimada, S.; Batsanov, A. S.; Lin, Z. Y.; Marder, T. B.; Cowan, J. A.; Howard, J. A. K.; Mason, S. A.; McIntyre, G. J. Organometallics 2003, 22, 4557.
8. (a) Männing, D.; Nöth, H. Angew. Chem, Int. Ed. Engl. 1985, 24, 878.
9. For reviews, see: (b) Burgess, K.; Ohlmeyer, M. J. Chem. Rev. 1991, 91, 1179.
10. (c) Burgess, K.; van der Donk, W. A. In Encyclopedia of Inorganic Chemistry; King, R. B., Ed.; Wiley: Chichester, U.K., 1994; Vol. 3, p 1420.
11. (d) Fu, G. C.; Evans, D. A.; Muci, A. R. In Advances in Catalytic Processes; Doyle, M. P., Ed.; JAI: Greenwich, CT, 1995; p 95.
12. (e) Beletskaya, I.; Pelter, A. Tetrahedron 1997, 53, 4957.
13. (f) Crudden, C. M.; Edwards, D. Eur. J. Org. Chem. 2003, 4695.
14. For recent reviews, see: (a) Marder, T. B.; Norman, N. C. Top. Catal. 1998, 5, 63.
15. (b) Ishiyama, T.; Miyaura, N. J. Synth. Org. Chem. Jpn. 1999, 57, 503.
16. (c) Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2000, 611, 392.
17. (d) Ishiyama, T.; Miyaura, N. Chem. Rec. 2004, 3, 271.
18. (a) Musaev, D. G.; Mebel, A. M.; Morokuma, K. J. Am. Chem. Soc. 1994, 116, 10693.
19. (b) Dorigo, A. E.; Schleyer, P. v. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 115.
20. (c) Widauer, C.; Grützmacher, H.; Ziegler, T. Organometallics 2000, 19, 2097.
21. For a review, see: (d) Huang, X.; Lin, Z. Y. In Computational Modeling of Homogeneous Catalysis; Maseras, F., Lledós, A., Eds.; Kluwer Academic Publishers: Amsterdam, The Netherlands, 2002; pp 189-212.
22. (a) Iverson, C. N.; Smith, M. R., III. J. Am. Chem. Soc. 1999, 121, 7696.
23. (b) Waltz, K. M.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 11358.
24. (c) Chen, H.; Schlecht, S.; Semple, T. C.; Hartwig, J. F. Science 2000, 287, 1995.
25. (d) Cho, J.-Y.; Iverson, C. N.; Smith, M. R., III. J. Am. Chem. Soc. 2000, 122, 12868.
26. (e) Tse, M. K.; Cho, J.-Y.; Smith, M. R., III. Org. Lett. 2001, 3, 2831.
27. (f) Ishiyama, T.; Ishida, K.; Takagi, J.; Miyaura, N. Chem. Lett. 2001, 1082.
28. (g) Cho, J.-Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E., Jr.; Smith, M. R., III. Science 2002, 295, 305.
29. (h) Ishiyama, T.; Tagaki, J.; Ishida, K.; Miyaura, N.; Anastasi, N. R.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 390.
30. (i) Kondo, Y.; Garica-Cuadrado, D.; Hartwig, J. F.; Boaen, N. K.; Wagner, N. L.; Hillmyer, M. A. J. Am. Chem. Soc. 2002, 124, 1164.
31. (j) Takagi, J.; Sato, K.; Hartwig, J. F.; Ishiyama, T.; Miyaura, N. Tetrahedron Lett. 2002, 43, 5649.
32. (k) Ishiyama, T.; Takagi, J.; Hartwig, J. F.; Miyaura, N. Angew. Chem., Int. Ed. 2002, 41, 3056.
33. (l) Wan, X.; Wang, X.; Luo, Y.; Takami, S.; Kubo, M.; Miyamoto, A. Organometallics 2002, 21, 3703.
34. (m) Webster, C. E.; Fan, Y.; Hall, M. B.; Kunz, D.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 858.
35. (n) Lam, W. H.; Lin, Z. Y. Organometallics 2003, 22, 473.
36. (o) Tamura, H.; Yamazaki, H.; Sato, H.; Sakaki, S. J. Am. Chem. Soc. 2003, 125, 16114.
37. (p) Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2003, 680, 3.
38. (q) Kurotobi, K.; Miyauchi, M.; Takakura, K.; Murafuji, T.; Sugihara, Y. Eur. J. Org. Chem. 2003, 3663.
39. (r) Ishiyama, T.; Nobuta, Y.; Hartwig, J. F.; Miyaura, N. Chem. Commun. 2003, 2924.
40. (s) Ishiyama, T.; Takagi, J.; Yonekawa, Y.; Hartwig, J. F.; Miyaura, N. Adv. Synth. Catal. 2003, 345, 1003.
41. (t) Ishiyama, T.; Datta, A.; Köllhofer, A.; Plenio, H. Chem. Commun. 2004, 1508.
42. (u) Lam, W. H.; Lam, K. C.; Lin, Z.; Shimada, S.; Perutz, R. N.; Marder, T. B. Dalton Trans. 2004, 1556.
43. (v) Ishiyama, T. J. Synth. Org. Chem. Jpn. 2005, 63, 440.
44. (w) Coventry, D. N.; Batsanov, A. S.; Goeta, A. E.; Howard, J. A. K. H.; Marder, T. B.; Perutz, R. N. Chem. Commun. 2005, 2172.
45. (x) Mkhalid, I. A. I.; Coventry, D. N.; Albesa-Jové, D.; Batsanov, A. S.; Howard, J. A. K.; Perutz, R. N.; Marder, T. B. Angew. Chem., Int. Ed. 2005. in press.
46. Rablen, P. R.; Hartwig, J. F.; Nolan, S. P. J. Am. Chem. Soc. 1994, 116, 4121.
47. (a) Cundari, T. R.; Zhao, Y. Inorg. Chim. Acta 2003, 345, 70.
48. (b) Frenking, G.; Frölich, N. Chem. Rev. 2000, 100, 717.
49. (c) Giju, K. T.; Bickelhaupt, F. M.; Frenking, G. Inorg. Chem. 2000, 39, 4776.
50. (d) Sakaki, S.; Biswas, B.; Musashi, Y.; Sugimoto, M. J. Organomet. Chem. 2000, 611, 288.
51. (e) Sakaki, S.; Kai, S.; Sugimoto, M. Organometallics 1999, 18, 4825.
52. (f) Sivignon, G.; Fleurat-Lassard, P.; Onno, J. M.; Volatron, F. Inorg. Chem. 2002, 41, 6656.
53. (g) Hartwig, J. F.; He, X. M. Organometallics 1996, 15, 5350.
54. (h) Hartwig, J. F.; Degala, S. R. J. Am. Chem. Soc. 1994, 116, 3661.
55. (a) Dickinson, A. A.; Willock, D. J.; Calder, R. J.; Aldridge, S. Organometallics 2002, 21, 1146.
56. (b) Braunschweig, H.; Radacki, K.; Seeler, F.; Whittell, G. R. Organometallics 2004, 23, 4178.
57. (c) Aldridge, S.; Calder, R. J.; Baghurst, R. E.; Light, M. E.; Hursthouse, M. B. J. Organomet. Chem. 2002, 649, 9.
58. Musaev, D. G.; Morokuma, K. J. Phys. Chem. 1996, 100, 6509.
59. Al-Fawaz, A.; Aldridge, S.; Coombs, D. L.; Dickinson, A. A.; Willock, D. J.; Li-ling Ooi, L.-L.; Light, M. E.; Coles, S. J.; Hursthouse, M. B. Dalton Trans. 2004, 4030.
60. (a) Lam, K. C.; Lam, W. H.; Lin, Z. Y.; Marder, T. B.; Norman, N. C. Inorg. Chem. 2004, 43, 2541.
61. For example, see also: (b) Braunschweig, H.; Radacki, K.; Rais, D.; Seeler, F. Organometallics 2004, 23, 5545.
62. (c) Braunschweig, H.; Radacki, K.; Rais, D. Scheschkewitz, D. Angew. Chem. 2005, 44, 5651.
63. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
64. (b) Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200.
65. (c) Lee, C.; Yang, W.; Parr, G. Phys. Rev. B 1988, 37, 785.
66. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299.
67. Huzinaga, S. Gaussian Basis Sets for Molecular Calculations; Elsevier Science Publishing Co.: Amsterdam, The Netherlands, 1984.
68. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomeperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. GAUSSIAN98, revision A.9; Gaussian, Inc.: Pittsburgh, PA, 1998.
69. (a) Clegg, W.; Lawlor, F. J.; Lesley, G.; Marder, T. B.; Norman, N. C.; Orpen, A. G.; Quayle, M. J.; Rice, C. R.; Scott, A. J.; Souza, F. E. S. J. Organomet. Chem. 1998, 550, 183.
70. (b) Curtis, D.; Lesley, M. J. G.; Norman, N. C.; Orpen, A. G.; Starbuck, J. J. Chem. Soc., Dalton Trans. 1999, 1687.
71. Purcell, K. F.; Kotz, J. C. Inorganic Chemistry; W. B. Saunders Co.: London, 1977.
72. Autschbach, J. Struct. Bonding (Berlin, Ger.) 2004, 112, 1.
73. Appleton, T. G.; Clark, H. C.; Manzer, L. E. Coord. Chem. Rev. 1973, 10, 335.
74. (a) Pidcock, A.; Richards, R. E.; Venanzi, L. M. J. Chem. Soc. A 1966, 1707.
75. (b) Venanzi, L. M. Chem. Brit. 1968, 4, 162.
76. Glendening, E. D.; Reed, A. E.; Carpenter, J. E.; Weihold, F. NBO, version 3.1.
77. Huheey, J. E.; Keiter, E. A.; Keiter, R. L. Inorganic Chemistry: Principles of Structure and Reactivity, 4th ed.; Harper Collins: New York, 1993; p 227.
78. Manojloviæ-Muir, L. J.; Muir, K. W. Inorg. Chim. Acta 1974, 10, 47.
79. (a) Schilling, B. E. R.; Hoffmann, R.; Lichtenberger, D. L. J. Am. Chem. Soc. 1979, 101, 585.
80. (b) Lichtenberger, D. L.; Renshaw, S. K.; Bullock, R. M. J. Am. Chem. Soc. 1993, 115, 3276.
81. (c) Lichtenberger, D. L.; Renshaw, S. K.; Wong, A.; Tagge, C. D. Organometallics 1993, 12, 3522.
82. (d) Lichtenberger, D. L.; Kellogg, G. E. Acc. Chem. Res. 1987, 20, 379.
83. For example, see: (a) Marciniec, B.; Gulinski, J.; Urbaniak, W.; Kornetka, Z. W. Comprehensive Handbook on Hydrosilylation; Pergamon Press: Oxford, U.K., 1992.
84. (b) Ojima, I. In The Chemistry of Organic Silicon Compounds; Patai, S., Rappoport, Z., Eds.; John Wiley & Sons: New York, 1989; pp 1479-1526.
85. (c) Lewis, L. N.; Stein, J.; Gao, Y.; Colborn, R. E.; Hutchins, G. Platinum Met. Rev. 1997, 41, 66.
86. (d) Noll, W. Chemistry and Technology of Silicones; Academic Press: New York, 1968.
87. (e) Auburn, M. J.; Stobart, S. R. Inorg. Chem. 1985, 24, 317.
88. (f) Auburn, M. J.; Holmes-Smith, R. D.; Stobart, S. R. J. Am. Chem. Soc. 1984, 106, 1314.
89. (g) Han, L. B.; Tanaka, M. Chem. Commun. 1999, 395.
90. (h) Onozawa, S.; Tanaka, M. J. Synth. Org. Chem. Jpn. 2002, 60, 826.
91. (i) Suginome, M.; Ito, Y. Chem. Rev. 2000, 100, 3221.
92. (j) Suginome, M.; Iwanami, T.; Ohmori, Y.; Matsumoto, A.; Ito, Y. Chem. - Eur. J. 2005, 11, 2954.
93. (k) Trost, B. M.; Ball, Z. T. Synthesis 2005, 6, 853.
94. (a) Douglas, B.; McDaniel, D.; Alexander, J. Concepts and Models of Inorganic Chemistry, 3rd ed.; John Wiley & Sons: New York, 1994; p 84.
95. (b) Rodgers, G. E. Introduction to Coordination, Solid State, and Descriptive Inorganic Chemistry; McGraw-Hill: New York, 1994; p 223.