Reaction of bis(alkynyl)silanes with tris(pentafluorophenyl)-borane: Synthesis of bulky silole derivatives by means of 1,1-carboboration under mild reaction conditions

Advanced Synthesis and Catalysis

Volumn 351, Issue 7-8, 2009, Pages 1080-1088

  Dierker, Gereon ^a   Ugolotti, Juri ^a   Kehr, Gerald ^a   Fröhlich, Roland ^a   Erker, Gerhard ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

1,1 carboboration; Boranes; Lewis acids; Siloles

Indexed keywords

EID: 66149139746     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200900029     Document Type: Article

References (115)

1. For recent reviews, see: a) S. Yamaguchi, K. Tamao, J. Chem. Soc. Dalton Trans. 1998, 3693-3702
2. And References therein; b) M. Hissler, P. W. Dyer, R. Reau, Coord. Chem. Rev. 2003, 244, 1-44;
3. c) B. Wrackmeyer, Heteroat. Chem. 2006, 17, 188-208.
4. See also: a) J. Dubac, A. Laporterie, G. Manuel, Chem. Rev. 1990, 90, 215-263;
5. b) E. Colomer, R. J. P. Corriu, M. Lheureux, Chem. Rev. 1990, 90, 265-282;
6. c) B. Wrackmeyer, Coord. Chem. Rev. 1995, 145, 125-156.
7. a) S. Yamaguchi, Y. Itami, K. Tamao, Organometallics 1998, 17, 4910-4916;
8. b) S. Yamaguchi, T. Endo, M. Uchida, T. Izumizawa, K. Furukawa, K. Tamao, Chem. Eur. J. 2000, 6, 1683-1692;
9. c) S. Yamaguchi, K. Tamao, Chem. Lett. 2005, 34, 2-7.
10. a) X. Zhan, C. Risko, F. Amy, C. Chan, W. Zhao, S. Barlow, A. Kahn, J.-L. Bredas, S. R. Marder, J. Am. Chem. Soc. 2005, 127, 9021-9029;
11. b) M. M. Sartin, A. J. Boydston, B. L. Pagenkopf, A. J. Bard, J. Am. Chem. Soc. 2006, 128, 10163-10170;
12. c) K. Geramita, J. McBee, Y. Shen, N. Radu, T. D. Tilley, Chem. Mater. 2006, 18, 3261-3269;
13. d) C. Booker, X. Wang, S. Haroun, J. Zhou, M. Jennings, B. L. Pagenkopf, Z. Ding, Angew. Chem. 2008, 120, 7845-7849;
14. Angew. Chem. Int. Ed. 2008, 47, 7731-7735.
15. V. N. Khabashesku, V. Balaji, S. E. Boganov, O. M. Ne-fedov, J. Michl, J. Am. Chem. Soc. 1994, 116, 320-329.
16. a) K. Tamao, S. Yamaguchi, Y. Ito, Y. Matsuzaki, T. Yamabe, M. Fukushima, S. Mori, Macromolecules 1995, 28, 8668-8675;
17. b) S. Yamaguchi, K. Tamao, Bull. Chem. Soc. Jpn. 1996, 69, 2327-2334;
18. c) K. Tamao, S. Ohno, S. Yamaguchi, Chem. Commun. 1996, 1873-1874.
19. See also: a) K. Tamao, M. Uchida, T. Izumizawa, K. Furukawa, S. Yamaguchi, J. Am. Chem. Soc. 1996, 118, 11974-11975;
20. b) S. Yamaguchi, K. Tamao, J. Organo-met. Chem. 2002, 653, 223-228;
21. c) J. Chen, C. C. W. Law, J. W. Y. Lam, Y. Dong, S. M. F. Lo, I. D. Williams, D. Zhu, B. Z. Tang, Chem. Mater. 2003, 15, 1535-1546;
22. d) J. Lee, Q.-D. Liu, M. Motala, J. Dane, J. Gao, Y. Kang, S. Wang, Chem. Mater. 2004, 16, 1869-1877;
23. e) J. Lee, Q.-D. Liu, D.-R. Bai, Y. Kang, Y. Tao, S. Wang, Organometallics 2004, 23, 6205-6213;
24. f) H. J. Tracy, J. L. Mullin, W. T. Klooster, J. A. Martin, J. Haug, S. Wallace, I. Rudloe, K. Watts, Inorg. Chem. 2005, 44, 2003-2011;
25. g) J. Lee, Y.-Y. Yuan, Y. Kang, W.-L. Jia, Z.-H. Lu, S. Wang, Adv. Funct. Mater. 2006, 16, 681-686;
26. h) G. Yu, S. Yin, Y. Liu, J. Chen, X. Xu, X. Sun, D. Ma, X. Zhan, Q. Peng, Z. Shuai, B. Tang, D. Zhu, W. Fang, Y. Luo, J. Am. Chem. Soc. 2005, 127, 6335-6346.
27. See also: i) C.-H. Zao, A. Wakamiya, Y. Inukai, S. Yamaguchi, J. Am. Chem. Soc. 2006, 128, 15934-15935;
28. j) H.-J. Son, W.-S. Han, J.-Y. Chun, C.-J. Lee, I-I. Han, J. Ko, S. O. Kang, Organometallics 2007, 26, 519-526;
29. k) H.-J. Son, W.-S. Han, J.-Y. Chun, S.-N. Kwon, J. Ko, S. O. Kang, Organometallics 2008, 27, 2464-2473;
30. l) S.-i. Otsuka, H. Fukumoto, T. Yamamoto, Bull. Chem. Soc. Jpn. 2008, 81, 536-538.
31. a) H. Sohn, M. J. Sailor, D. Magde, W. C. Trogler, J. Am. Chem. Soc. 2003, 125, 3821-3830;
32. b) S. J. Toal, W.C. Trogler, J. Mater. Chem. 2006, 16, 2871-2883;
33. c) J. C. Sanchez, A. G. DiPasquale, A. L. Rheingold, W. C. Trogler, Chem. Mater. 2007, 19, 6459-6470.
34. a) E. H. Braye, W. Hiibel, Chem. Ind. (London) 1959, 1250-1251;
35. b) E. H. Braye, W. Hiibel, I. Caplier, J. Am. Chem. Soc. 1961, 83, 4406-4413.
36. a) P. Jutzi, A. Karl, J. Organomet. Chem. 1981, 214, 289-302;
37. b) U. Losehand, N. W Mitzel, J. Chem. Soc. Dalton Trans. 2000, 1049-1052.
38. a) T. Hiiro, N. Kambe, A. Ogawa, N. Miyoshi, S. Murai, N. Sonoda, Angew. Chem. 1987, 99, 1221-1222;
39. Angew. Chem. Int. Ed. Engl. 1987, 26, 1187-1188;
40. b) M. Katkevics, S. Yamaguchi, A. Toshimitsu, K. Tamao, Organometallics 1998, 17, 5796-5800.
41. C. Wang, Q. Luo, H. Sun, X. Guo, Z. Xi, J. Am. Chem. Soc. 2007, 129, 3094-3095.
42. a) K.-L. Kanno, M. Kira, Chem. Lett. 1999, 1127-1128;
43. see also: b) P. J. Fagan, W. A. Nugent, J. C. Calabrese, J. Am. Chem. Soc. 1994, 116, 1880-1889;
44. c) Y. Ura, Y. Li, Z. Xi, T. Takahashi, Tetrahedron Lett. 1998, 39, 2787-2790;
45. d) Z. Xi, Z. Li, Top. Organomet. Chem. 2004, 8, 27-56; and references cited therein.
46. a) S. Yamaguchi, R.-Z. Jin, S. Ohno, K. Tamao, Organometallics 1998, 17, 5133-5138;
47. b) S. Yamaguchi, R.-Z. Jin, K. Tamao, F. Sato, J. Org. Chem. 1998, 63, 10060-10062;
48. c) J. Braddock-Wilking, Y. Zhang, J. Y. Corey, N. P. Rath, J. Organomet. Chem. 2008, 693, 1233-1242;
49. d) T. Matsuda, Y. Yamaguchi, M. Murakami, Synlett 2008, 561-564.
50. See, for example: a) M. Horáček, N. Bazyakina, P. Štěpnička, R. Gyepes, I. Císařová, S. Bredeau, P. Meunier, J. Kubišta, K. Mach, J. Organomet. Chem. 2001, 628, 30-38;
51. b) T. Yu, X. Sun, C. Wang, L. Deng, Z. Xi, Chem. Eur. J. 2005, 11, 1895-1902;
52. c) C. K. Jin, T. Yamada, S. Sano, M. Shiro, Y. Nagao, Tetrahedron Lett. 2007, 48, 3671-3675;
53. d) J. Liu, W.-X. Zhang, X. Guo, Z. Hou, Z. Xi, Organometallics 2007, 26, 6812-6820;
54. e) J. Liu, S. Zhang, W.-X. Zhang, Z. Xi, Organometallics 2009, 28, 413-417, and references cited therein.
55. K. Tamao, S. Yamaguchi, M. Shiro, J. Am. Chem. Soc. 1994, 116, 11715-11722.
56. a) A. Sundararaman, M. Victor, R. Varughese, F. Jäkle, J. Am. Chem. Soc. 2005, 127, 13748-13749;
57. b) A. Wakamiya, T. Taniguchi, S. Yamaguchi, Angew. Chem. 2006, 118, 3242-3245;
58. Angew. Chem. Int. Ed. 2006, 45, 3170-3173;
59. c) A. Sundararaman, R. Varughese, H. Li, L. N. Zakharov, A. L. Rheingold, F. Jakle, Organometallics 2007, 26, 6126-6131;
60. d) H. Li, A. Sundararaman, K. Venkatasubbaiah, F. Jäkle, J. Am. Chem. Soc. 2007, 129, 5792-5793;
61. e) A. Wakamiya, K. Mori, S. Yamaguchi, Angew. Chem. 2007, 119, 4351-4354;
62. Angew. Chem. Int. Ed. 2007, 46, 4273-4276;
63. f) C.-H. Zao, A. Wakamiya, S. Yamaguchi, Macromolecules 2007, 40, 3898-3900;
64. g) S. L. Hellstrom, J. Ugolotti, G. J. P. Bri-tovsek, T. S. Jones, A. J. P. White, New J. Chem. 2008, 32, 1379-1387;
65. h) A. Fukazawa, H. Yamada, S. Yamaguchi, Angew. Chem. 2008, 120, 5664-5667;
66. Angew. Chem. Int. Ed. 2008, 47, 5582-5585;
67. i) M. Elbing, G. Bazan, Angew. Chem. 2008, 120, 846-850;
68. Angew. Chem. Int. Ed. 2008, 47, 834-838;
69. j) C.-W So, D. Wata-nabe, A. Wakamiya, S. Yamaguchi, Organometallics 2008, 27, 3496-3501.
70. a) B. Wrackmeyer, J. Chem. Soc. Chem. Commun. 1986, 397-399;
71. b) A. Sebald, P. Seiberlich, B. Wrackmeyer, J. Organomet. Chem. 1986, 303, 73-81.
72. a) L. Killian, B. Wrackemeyer, J. Organomet. Chem. 1977, 132, 213-221;
73. b) A. Sebald, B. Wrackmeyer, J. Chem. Soc. Chem. Commun. 1983, 1293-1294.
74. a) B. Wrackmeyer, C. Bihlmayer, J. Chem. Soc. Chem. Commun. 1981, 1093-1094;
75. b) B. Wrackmeyer, Rev. Silicon, Germanium, Tin, Lead Compd. 1982, 6, 75-148;
76. c) B. Wrackmeyer, G. Kehr, J. Süß, Chem. Ber. 1993, 126, 2221-2226;
77. d) R. Köster, G. Seidel, J. Süß, B. Wrackmeyer, Chem. Ber. 1993, 126, 1107-1114;
78. e) B. Wrackmeyer, G. Kehr, J. Süß, E. Molla, J. Organomet. Chem. 1998, 562, 207-215;
79. f) B. Wrackmeyer, O. L. Tok, K. Shahid, S. Ali, Inorg. Chim. Acta 2004, 357, 1103-1110.
80. a) B. Wrackmeyer, W. Milius, E.V. Klimkina, Y. N. Bubnov, Chem. Eur. J. 2001, 7, 775-782;
81. b) B. Wrackmeyer, W. Milius, O. L. Tok, Y. N. Bubnov, Chem. Eur. J. 2002, 8, 1537-1543;
82. c) B. Wrackmeyer, M. H. Bhatti, S. Ali, O. L. Tok, Y. N. Bubnov, J. Organomet. Chem. 2002, 657, 146-154.
83. a) V. V. Korshak, A. M. Sladkov, L. K. Luneva, Russ. Chem. Bull. 1962, 11, 677;
84. b) S. D. Ibekwe, M. J. New-lands, J. Chem. Soc. 1965, 4608-4610.
85. a) U. Krüerke, J. Organomet. Chem. 1970, 21, 83-90;
86. b) W-Y Wong, A. W.-M. Lee, C.-K. Wong, G.-L. Lu, H. Zhang, T. Mo, K.-T. Lam, New J. Chem. 2002, 26, 354-360;
87. c) M. Horáček, P. Štěpnička, R. Gyepes, I. Císařová, J. Kubišta, L. Lukešová, P. Meunier, K. Mach, Organometallics 2005, 24, 6094-6103.
88. a) A. G. Massey, A. J. Park, F. G. A. Stone, Proc. Chem. Soc. 1963, 212;
89. b) A. G. Massey, A. J. Park, J. Organomet. Chem. 1964, 2, 245-250;
90. c) G. Erker, Dalton Trans. 2005, 1883-1890.
91. 3 see for example: a) M. A. Beckett, G. C. Strickland, J. R. Holland, K. S. Varma, Polym. Commun. 1996, 37, 4629-4631;
92. b) M. A. Beckett, D.S. Brassington, S. J. Coles, M. B. Hursthouse, Inorg. Chem. Commun. 2000, 3, 530-533;
93. c) G. J. P. Britovsek, J. Ugolotti, A. J. P. White, Organometallics 2005, 24, 1685-1691.
94. See for a comparison: B. Wrackmeyer, Annual Reports on NMR Spectroscopy 2006, 57, 1-49.
95. a) B. Wrackmeyer, Nuclear Magnetic Resonance Spectroscopy of Boron Compounds Containing Two-, Three-and Four-Coordinated Boron, in: Annual Reports on NMR Spectroscopy, (Ed.: G. A. Webb), Academic Press, London, 1988, Vol. 20, pp 61-203;
96. b) D. Va-gedes, G. Erker, R. Fröhlich, Angew. Chem. 1999, 111, 3561-3565;
97. Angew. Chem. Int. Ed. 1999, 38, 3362-3364;
98. c) G. Erker, S. Venne-Dunker, G. Kehr, N. Klei-grewe, R. Fröhlich, C. Mück-Lichtenfeld, S. Grimme, Organometallics 2004, 23, 4391-4395;
99. d) C. Herrmann, G. Kehr, R. Fröhlich, G. Erker, Organometallics 2008, 27, 2328-2336;
100. e) P. Spies, R. Fröhlich, G. Kehr, G. Erker, S. Grimme, Chem. Eur. J. 2008, 14, 333-343;
101. Chem. Eur. J. 2008, 14, 779;
102. f) T. Beringhelli, D. Donghi, D. Maggioni, G. D'Alfonso, Coord. Chem. Rev. 2008, 252, 2292-2313.
103. See for a comparison: a) W. Ahlers, B. Temme, G. Erker, R. Fröhlich, T. Fox, J. Organomet. Chem. 1997, 527, 191-201;
104. b) D. Vagedes, G. Erker, G. Kehr, K. Bergander, O. Kataeva, R. Fröhlich, S. Grimme, C. Mück-Lichtenfeld, Dalton Trans. 2003, 1337-1344.
105. a) D. C. Bradley, I. S. Harding, A. D. Keefe, M. Mote-valli, D. H. Zheng, J. Chem. Soc. Dalton Trans. 1996, 3931-3936;
106. b) H. Jacobsen, H. Berke, S. Döring, G. Kehr, G. Erker, R. Fröhlich, O. Meyer, Organometallics 1999, 18, 1724-1735;
107. c) T. Beringhelli, D. Maggioni, G. D'Alfonso, Organometallics 2001, 20, 4927-4938.
108. J. Ugolotti, G. Kehr, R. Fröhlich, S. Grimme, G. Erker, J. Am. Chem. Soc. 2009, 131, 1996-2007.
109. M. M. Corradi, G. Jimenez Pindado, M. J. Sarsfield, M. Thornton-Pett, M. Bochmann, Organometallics 2000, 19, 1150-1159.
110. J. Ugolotti, G. Dierker, G. Kehr, R. Fröhlich, S. Grimme, G. Erker, Angew. Chem. 2008, 120, 2662-2665;
111. Angew. Chem. Int. Ed. 2008, 47, 2622-2625.
112. Z. Otwinowski, W. Minor, Methods in Enzymology, 1997, 276, 307-326.
113. Z. Otwinowski, D. Borek, W. Majewski, W. Minor, Acta Crystallogr. 2003, A59, 228-234.
114. G M. Sheldrick, Acta Crystallogr. 1990, A46, 467-473.
115. G M. Sheldrick, Acta Crystallogr. 2008, A64, 112-122.