Highly Lewis acidic bifunctional organoboranes

European Journal of Inorganic Chemistry

Volumn , Issue 10, 2000, Pages 2131-2142

  Piers, Warren E ^a   Irvine, Geoffrey J ^b   Williams, V Clifford ^b  

^a UNIVERSITY OF CALGARY   (Canada)

^b UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

Anions; Boranes; Lewis acids; Metallocenes

Indexed keywords

BORON; BORON COMPOUNDS; INDIUM COMPOUNDS; ORGANOMETALLICS;

BI-FUNCTIONAL; BIDENTATE LEWIS ACID; BORANE; DONOR GROUPS; LEWIS ACID; LEWIS ACIDIC; LEWIS BASE; MULTIDENTATE; ORGANO-BORANES; SELECTIVE BINDING;

NEGATIVE IONS;

ANION; BORANE DERIVATIVE; ORGANOBORON DERIVATIVE;

ANION TRANSPORT; CATALYSIS; CHELATION; DECOMPOSITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; SHORT SURVEY; STRUCTURE ANALYSIS; SYNTHESIS; THERMODYNAMICS; X RAY ANALYSIS;

EID: 0033770469     PISSN: 14341948     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0682(200010)2000:10<2131::AID-EJIC2131>3.0.CO;2-H     Document Type: Short Survey

References (96)

1. [1a] J. Vaugeois, M. Simard, J. D. Wuest, Coord. Chem. Rev. 1995, 145, 55-73.
2. [1b] J. D. Wuest, Acc. Chem. Res. 1999, 32, 81-89.
3. Multifunctional boranes with donating substituants are not part of the scope of this review. For leading references see:
4. [2a] G. J. Irvine, M. J. G. Lesley, T. B. Marder, N. C. Norman, C. R. Rice, E. G. Robins, W. R. Roper, G. R. Whittell, L. J. Wright, Chem. Rev. 1998, 98, 2685-2723.
5. [2b] G. Lesley, T. B. Marder, N. C. Norman, C. R. Rice, Main Group Chem. News 1998, 5, 4-11.
6. [2c] K. Nozaki, M. Yoshida, H. Takaya, Bull Chem. Soc. Jpn. 1996, 69, 2043-2052.
7. [2d] A. Maderna, H. Pritzkow, W. Siebert, Angew. Chem. Int. Ed Engl. 1996, 35, 1501-1503.
8. [2e] M. Bluhm, A. Maderna, H. Pritzkow, S. Bethke, R. Gleiter, W. Siebert, Eur. J. Inorg. Chem. 1999, 1693-1700.
9. [2f] T. Ishiyama, S. Momota, N. Miyaura, Synlett 1999, 1790-1792.
10. [2g] C. N. Iverson, M. R. Smith, III, Organometallics 1997, 16, 2757-2759.
11. [3a] T. Ooi, M. Takahashi, K. Maruoka, Angew. Chem. Int. Ed. 1998, 37, 835-837.
12. [3b] T. Ooi, T. Miura, K. Maruoka, Angew. Chem. Int. Ed 1998, 37, 2347-2349.
13. [4a] J. Vaugeois, J. D. Wuest, J. Am. Chem. Soc. 1998, 120, 13016-13022.
14. [4b] M. Tschinkl, A. Schier, J. Riede, F. P. Gabbaï, Organometallics 1999, 18, 1747-1753.
15. [4c] M. Tschinkl, A. Schier, J. Riede, F. P. Gabbaï, Angm: Chem. Int. Ed 1999, 38, 3547-3549.
16. N. Asao, P. Liu, K. Maruoka, Angew. Chem. Int. Ed Engl. 1997, 36, 2507-2509.
17. N. Asao, S. Kii, H. Hanawa, K. Maruoka, Tetrahedron Lett. 1998, 39, 3729-3732.
18. A. G. Massey, A. J. Park, J. Organontet. Chem. 1964, 2, 245-250.
19. [8a] A. G. Massey, A. J. Park, J. Organomet. Chem. 1966, 5, 218-225.
20. [8b] L. Doerrer, M. L. H. Green, J. Chem. Soc., Dalton Trans. 1999, 4325-4329.
21. L. Luo, T. J. Marks, Topics in Catalysis 1999, 7, 97-106.
22. H. Jacobsen, H. Berke, S. Döring, G. Kehr, G. Erker, R. Fröhlich, O. Meyer, Organometallics 1999, 18, 1724-1735.
23. W. E. Piers, T. Olivers, Chem. Soc. Rev. 1997, 345-354.
24. H. Yamamoto, K. Ishihara, Eur. J. Org. Chem. 1999, 527-538.
25. [13a] P. D. Beer, Chem. Commun. 1996, 689-696.
26. [13b] M. F. Hawthorne, Z. Zheng, Acc. Chem. Res. 1997, 30, 267-276.
27. M. Fontani, F. Peters, W. Scherer, W. Wachter, M. Waaner, P. Zanello, Eur. J. Inorg. Chem. 1998, 1453-1465.
28. [15a] G. A. Olah, Angew Chem. Int Ed Eng, 1993, 32, 761-788.
29. [5b] E. Negishi, Chem. Eur. J. 1999, 5, 411-423.
30. W. Clegg, C. Dai, F. J. Lawlor, T. B. Marder, R Nguyen, N. C. Norman, N. L. Pickett, W. P. Power, A. J. Scott, J. Chem. Soc., Dalton Trans. 1997, 839-846.
31. [19a] D. F. Shriver, M. J. Biallas, J. Am. Chem. Soc. 1967, 59, 1078-1081.
32. [17b] M. J. Biallas, J. Am. Chem. Soc. 1969, 91, 7290-7292.
33. [17c] M. J. Biallas, Inorg. Chem. 1971, 10, 1320-1322.
34. P. Ceron, A. Finch, J. Frey, J. Kerrigan, T. Parsons, G. Urry, H. I. Schlesinger, J. Am. Chem. Soc. 1959, 81, 6368-6371.
35. H. E. Katz, J. Org. Chem. 1985, 50, 5027-5032.
36. H. E. Katz, Organometallics 1987, 6, 1136-1138.
37. M. Reilly, T. Oh, Tetrahedron Lett. 1994, 35, 7209-7212.
38. [22a] R. Köster, G Seidel, K. Wagner, B. Wrackmeyer, Chem. Ber. 1993, 126, 305-317, and references therein.
39. [22b] R. Köster, G. Seidel, B. Wrackmeyer, Chem. Ber. 1993, 726, 319-330, and references therein.
40. [23a] W. Siebert, M. Hildenbrand, P. Hornbach, G. Karger, H. Pritzkow, Z. Naturforsclt, B: Chem. Sei. 1989, 44, 1179-1186.
41. [23b] H. Schultz, G. Gabbert, H. Pritzkow, W. Siebert, Chem. Ber. 1993, 126, 1593-1595.
42. W. Schacht, D. E. Kaufmann, J. Organomet. Chem. 1987, 331, 139-152.
43. D. E. Kaufmann, Chem. Ber. 1987, 720, 901-905.
44. J. J. Eisch, B. W. Kotowicz, Eur. J. Inorg. Chem. 1998, 761 -769.
45. L. Jia, X. Yang, C. L. Stern, T. J. Marks, Organometallics 1994, 13, 3755-3757.
46. [28a] D. J. Parks, R. E. v H. Spence, W. E. Piers, Angew. Chem. Int. Ed Engl. 1995, 34, 809-811.
47. [28b] D. J. Parks, W. E. Piers, G. P. A. Yap, Organometallics 1998, 17, 5492-5503.
48. K. Köhler, W. E. Piers, Can. J. Chem. 1998, 76, 1249-1255.
49. [30a] R. E. v H. Spence, W. E. Piers, Y. Sun, M. Parvez, L. R. MacGillivray, M. J. Zaworotko, Organometallics 1998, 17, 2459-2469.
50. [30b] K. S. Cook, W. E. Piers, S. J. Rettig, Organometallics 1999, 18, 1575-1577.
51. For examples of 1,1′-diboryl alkenes incorporating halogen substituents, see ref.[23a] and: H. Schultz, H. Pritzkow, W. Siebert, Z. Naturforsclt 1993, 48b, 719-722.
52. K. Köhler, W. E. Piers, A. P. Jarvis, S. Xin, Y. Feng, A. M. Bravakis, S. Collins, W. Clegg, G. P. A. Yap, T. B. Marder, Organometallics 1998, 17, 3557-3566.
53. [33a] S. Krishnamurthy, H. C. Brown, J. Org. Chem. 1980, 45, 849-856.
54. [33b] T. Yoshida, E. Negishi, J. Chem. Soc., Chem. Commun. 1974, 762-763.
55. [33c] A. Pelter, K. Smith, H. C. Brown, Borane Reagents, Academic Press, New York, 1988, 22-23.
56. J. R. Galsworthy, M. L. H. Green, V. C. Williams, A. N. Chernega, Polyhedron 1998, 17, 119-124.
57. S. Collins, J. Tian, N. J. Taylor, unpublished results.
58. Spartan Version 3.1, Wavefunction Inc., Irvine, California.
59. T. J. Marks, L. Jia, X. Yang, U. S. Patent 5,447,895, 1995 (Northwestern University).
60. D. J. Parks, W. E. Piers, Tetrahedron 1998, 54, 15469-15488.
61. 2, 300 K): δ = 41.4, 5.7. G. J. Irvine, L. Somlai, W. E. Piers, unpublished results.
62. V. C. Williams, W. E. Piers, W. Clege, S. Collins, T. B. Marder, J. Am. Chem.. Soc. 1999, 727, 3244-3245.
63. 4.[26] To avoid Me transfer to boron we therefore prepared it from the arylsilane precursor, and to suppress condensation of the product to the 9,10-diboraanthracene, we minimized the heating of the chloroborane during purification and workup.
64. P. Sartori, M. Weidenbruch, Chem. Ber. 1967, 700, 3016-3023.
65. Y. Sun, W. E. Piers, M. Parvez, Can. J. Chem. 1998, 76, 513-517.
66. P. A. Deck, C. L. Beswick, T. J. Marks, J. Am. Chem. Soc. 1998,720, 1772-1784.
67. T. Chivers, J. Organomet. Chem.. 1969, 79, 75-80.
68. R. D. Chambers, T. Chivers, J. Chem. Soc. 1965, 3933-3939.
69. [47a] M. H. Mcadon, R M. Nickias, T. J. Marks, D. J. Schwartz, WO 99/06413, 1999 (Dow Chemical Co. and Northwestern University).
70. [47b] M. V. Metz, D. J. Schwartz, C. L. Stern, P. N. Nickias, T. J. Marks, Angew. Chem. Int. Ed. 2000, 39, 1312.
71. [47c] T. J. Marks, Abstracts of the 217th National ACS Meeting, 1999, Anaheim, CA, #0015.
72. R Sartori, A. Golloch, Chem. Ber. 1968, 707, 2004-2009.
73. R. D. Chambers, T. Chivers, J. Chem. Soc. 1964, 4782-4790.
74. M. Tschinkl, R. E. Bachman, F. P. Gabbäi, Chem. Commun. 1999, 1367-1368.
75. For a related study see: J. J. Eisch, K. Mackenzie, H. Windsich, C. Krüger, Eur. J. Inorg. Chem. 1999, 153-162, and references therein.
76. [52a] p p Gabbaï, A. Schier, J. Riede, D. Schichl, Organometallics 1996, 75, 4119-4121.
77. [52b] F. P. Gabbaï, A. Schier, J. Riede, Angew. Chem. Int. Ed. 1998, 37, 622-624.
78. V. C. Williams, C. Dai, Z. Li, S. Collins, W. E. Piers, W. Clegg, M. R. J. Elsegood, T. B. Marder, Augew. Chem. Int. Ed. 1999, 38, 3695-3698.
79. M. Bochmann, S. L. Lancaster, Augen: Chem. Int. Ed. Engl. 1994, 33, 1634-1637.
80. X. Yang, C. L. Stern, T. J. Marks, J. Am. Chem. Soc. 1994, 116, 10015-10031.
81. This structure determination was obtained subsequent to publication of our initial report. V. C. Williams, W. E. Piers, W. Clegg, M. R. J. Elsegood, unpublished results.
82. V. C. Williams, G. J. Irvine, W. E. Piers, Z. Li, S. Collins, W. Clegg, M. R. J. Elsegood, T. B. Marder, Organometallics 2000, 19, 1619.
83. W. E. Piers, V. C. Williams, G. J. Irvine, S. Collins, C. Dai, Z. Li, W. Clegg, M. R. J. Elsegood, Abstracts of the 218th National ACS Meeting, 1999, New Orleans, LA, #295.
84. A shift of δ = -88.3 was observed for the μ-F group in this cation with a different counteranion: L. Li, T. J. Marks, Organometallics 1998, 77, 3996-4003.
85. 20Si (776.07): calcd. C 43.2, H 1.3; found C 43.0, H 1.0.
86. [61a] W. R. Tikkanen, J. Z. Liu, J. W. Egan, Jr., J. L. Petersen, Organometallics 1984, 3, 825-830.
87. [61b] W. R. Tikkanen, J. W. Egan, Jr., J. L. Petersen, Organometallics 1984, 3, 1646-1650.
88. D. Haussinger, M. Muller, M. L. H. Green, XVIIIth Interna-tional Conference on Orgaiioinetallic Chemistry, 1998, Munich, Germany.
89. G. E. Herberich, U. Englert, A. Fischer, D. Wiebelhaus, Organonietallics 1998, 17, 4769-4775.
90. M. D. Rausch, L.P. Klemann, A. Siegel, R. F. Kovar, T. H. Gund, Synth. Reactiv. Inorg. Metal-Org. Chem. 1973, 3, 193-198.
91. B. E. Carpenter, M. Sc. Thesis, University of Calgary, 1999.
92. B. Schilling, V. Kaiser, D. E. Kaufmann, Chem. Ber./Recueil 1997,130, 923-932.
93. [67a] D. J. Parks, W. E. Piers, J. Am. Chem. Soc. 1996, 118, 9440-9441.
94. [67b] J. M. Blackwell, K. L. Foster, V. H. Beck, W. E. Piers, J. Org. Chem. 1999, 64, 4887-4892.
95. [67c] J. M. Blackwell, W. E. Piers, M. Parvez, Org. Lett. 2000, 2, 695-698.
96. Received February 11, 2000 [100047]