Reduction of phenyl silyl acetylenes with lithium: Unexpected formation of a dilithium dibenzopentalenide

Angewandte Chemie - International Edition

Volumn 46, Issue 9, 2007, Pages 1504-1507

  Saito, Masaichi ^a   Nakamura, Michio ^a   Tajima, Tomoyuki ^a   Yoshioka, Michikazu ^a  

^a SAITAMA UNIVERSITY   (Japan)

Author keywords

Alkynes; Aromatic systems; Intermolecular cyclization; Metalation; Reduction

Indexed keywords

ACETYLENE; AROMATIC COMPOUNDS; CYCLIZATION; REDUCTION;

AROMATIC SYSTEMS; INTERMOLECULAR CYCLIZATION; METALATION;

LITHIUM;

EID: 34250711880     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200604067     Document Type: Article

References (47)

1. a) L. I. Smith, H. H. Hoehn, J. Am. Chem. Soc. 1941, 63, 1184;
2. b) A. G. Evans, J. C Evans, P. J. Emes, T. J. Phelan, J. Chem. Soc. B 1971, 315;
3. c) Z. Csürös, P. Caluwe, M. Szwarc, J. Am. Chem. Soc. 1973, 95, 6171;
4. d) Z. Xi, Eur. J. Org. Chem. 2004, 2773.
5. For a review, see: J. Dubac, A. Laporterie, G. Manuel, Chem. Rev. 1990, 90, 215.
6. a) A. J. Ashe III, J. W. Kampf, P. M. Savla, Organometallics 1993, 12, 3350;
7. b) F. Pauer, P. P. Power, J. Organomet. Chem. 1994, 474, 27.
8. For the first synthesis of a dilithium salt of pentalene, see: a) T. J. Katz, M. Rosenberger, J. Am. Chem. Soc. 1962, 84, 865;
9. b) T. J. Katz, M. Rosenberger, R. K. O'Hara, J. Am. Chem. Soc. 1964, 86, 249.
10. a) S. C. Jones, D. O'Hare, Chem. Commun. 2003, 2208;
11. b) S. C. Jones, T. Hascall, A. J. Norquist, D. O'Hare, Inorg. Chem. 2003, 42, 7707;
12. c) F. Cloke, N. Geoffrey, P. B. Hitchcock, M. C. Kuchta, N. A. Morley-Smith, Polyhedron 2004, 23, 2625.
13. For some reviews, see: a) R. E. Martin, F. Diederich, Angew. Chem. 1999, 111, 1440;
14. Angew. Chem. Int. Ed. 1999, 38, 1350;
15. b) U. Scherf, J. Mater. Chem. 1999, 9, 1853;
16. c) M. D. Watson, A. Fechtenkötter, K. Mullen, Chem. Rev. 2001, 101, 1267.
17. For dihydropentalene derivatives, see: a) J. Saltiel, O. C. Zafiriou, E. D. Megarity, A. A. Lamola, J. Am. Chem. Soc. 1968, 90, 4759;
18. b) J. Saltiel, A. Marinari, D. W. L. Chang, J. C. Mitchener, E. D. Megarity, J. Am. Chem. Soc. 1979, 101, 2982.
19. For a silicon analogue of dihydropentalene, see: S. Yamaguchi, C. Xu, K. Tamao, J. Am. Chem. Soc. 2003, 125, 13662.
20. a) M. Saito, R. Haga, M. Yoshioka, Chem. Commun. 2002, 1002;
21. b) M. Saito, R. Haga, M. Yoshioka, Chem. Lett. 2003, 32, 912;
22. c) M. Saito, R. Haga, M. Yoshioka, Phosphorus Sulfur Silicon Relat. Elem. 2004, 179, 703;
23. d) M. Saito, R. Haga, M. Yoshioka, K. Ishimura, S. Nagase, Angew. Chem. 2005, 117, 6711;
24. Angew. Chem. Int. Ed. 2005, 44, 6553;
25. e) M. Saito, M. Yoshioka, Coord. Chem. Rev. 2005, 249, 765;
26. f) R. Haga, M. Saito, M. Yoshioka, J. Am. Chem. Soc. 2006, 128, 4934.
27. T. P. Vaid, A. S. Veige, E. B. Lobkovsky, W. V. Glassey, P. T. Wolczanski, L. M. Liable-Sands, A. L. Rheingold, T. R. Cundari, J. Am. Chem. Soc. 1998, 120, 10067.
28. For experimental details, see the Supporting Information.
29. T. K. Jones, S. E. Denmark, Helv. Chim. Acta 1983, 66, 2397.
30. CCDC-622259 (4), CCDC-622261 (5), CCDC-622260 (7), CCDC-622263 (9), and CCDC-622262 (10) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data_request/cif.
31. Y. Badrieh, A. Greenwald, H. Schumann, J. Blum, Chem. Ber. 1992, 125, 667.
32. a) H. Jiao, P. von R. Schleyer, Y. Mo, M. A. McAllister, T. T. Tidwell, J. Am. Chem. Soc. 1997, 119, 7075;
33. b) S.-B. Choi, P. Boudjouk, P. Wei, J. Am. Chem. Soc. 1998, 120, 5814;
34. c) S.-B. Choi, P. Boudjouk, K. Qin, Organometallics 2000, 19, 1806;
35. d) Y. Liu, T. C. Stringfellow, D. Ballweg, I. A. Guzei, R. West, J. Am. Chem. Soc. 2002, 124, 49;
36. e) Y. Liu, D. Ballweg, T. Müller, I. A. Guzei, R. W. Clark, R. West, J. Am. Chem. Soc. 2002, 124, 12174;
37. f) M. Saito, M. Shimosawa, M. Yoshioka, K. Ishimura, S. Nagase, Organometallics 2006, 25, 2967;
38. g) M. Saito, M. Shimosawa, M. Yoshioka, K. Ishimura, S. Nagase, Chem. Lett. 2006, 35, 940.
39. a) I. Willner, M. Rabinovitz, J. Am. Chem. Soc. 1978, 100, 337;
40. b) I. Willner, J. Y. Becker, M. Rabinovitz, J. Am. Chem. Soc. 1979, 101, 395.
41. a) M. Jones, L. O. Schwab, J. Am. Chem. Soc. 1968, 90, 6549;
42. b) H. Meier, A. Pauli, P. Kochhan, Synthesis 1987, 573.
43. It was concluded that the tert-butyldimethylsilyl group is less bulky than the triisopropylsilyl group from the rate of alcoholysis of the corresponding chlorides; see: N. Shimizu, N. Takesue, S. Yasuhara, T. Inazu, Chem. Lett. 1993, 22, 1807.
44. The configuration of 10 was determined to be Z,Z by X-ray crystallographic analysis.
45. H. Köster, D. Thoennes, E. Weiss, J. Organomet. Chem. 1978, 160, 1.
46. H. Dietrich, Acta Crystallogr. 1963, 16, 681.
47. J. T. B. H. Jastrzebski, G. van Koten, M. Konijn, C. H. Stam, J. Am. Chem. Soc. 1982, 104, 5490.