Alkene addition of frustrated P/B and N/B Lewis pairs at the [3]ferrocenophane framework

Organometallics

Volumn 30, Issue 3, 2011, Pages 584-594

  Voss, Tanja ^a   Sortais, Jean Baptiste ^a   Fröhlich, Roland ^a   Kehr, Gerald ^a   Erker, Gerhard ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

FERROCENOPHANES; INTRAMOLECULAR ADDITIONS; MULTI-STEP; SYNTHETIC PATHWAYS; WITTIG OLEFINATION;

ADDITION REACTIONS; ALDEHYDES; BUTADIENE; X RAY DIFFRACTION;

OLEFINS;

EID: 79751517190     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om100949k     Document Type: Article

References (67)

1. Wittig, G.; Benz, E. Chem. Ber. 1959, 92, 1999-2013
2. Tochtermann, W. Angew. Chem. 1966, 78, 355-375
3. Angew. Chem., Int. Ed. 1966, 5, 351-371.
4. McCahill, J. S. J.; Welch, G. C.; Stephan, D. W. Angew. Chem. 2007, 119, 5056-5059
5. Angew. Chem., Int. Ed. 2007, 46, 4968-4971.
6. Mömming, C. M.; Frömel, S.; Kehr, G.; Fröhlich, R.; Grimme, S.; Erker, G. J. Am. Chem. Soc. 2009, 131, 12280-12289
7. Sortais, J.-B.; Voss, T.; Kehr, G.; Fröhlich, R.; Erker, G. Chem. Commun. 2009, 7417-7418
8. Voss, T.; Chen, C.; Kehr, G.; Nauha, E.; Erker, G.; Stephan, D. W. Chem. Eur. J. 2010, 16, 3005-3008
9. Dureen, M. A.; Stephan, D. W. J. Am. Chem. Soc. 2009, 131, 8396-8397
10. Mömming, C. M.; Kehr, G.; Wibbeling, B.; Fröhlich, R.; Schirmer, B.; Grimme, S.; Erker, G. Angew. Chem. 2010, 122, 2464-2467
11. Angew. Chem., Int. Ed. 2010, 49, 2414-2417.
12. Jiang, C.; Blacque, O.; Berke, H. Organometallics 2010, 29, 125-133
13. Chen, C.; Fröhlich, R.; Kehr, G.; Erker, G. Chem. Commun. 2010, 46, 3580-3582
14. Chen, C.; Eweiner, F.; Wibbeling, B.; Fröhlich, R.; Senda, S.; Ohki, Y.; Tatsumi, K.; Grimme, S.; Kehr, G.; Erker, G. Chem. Asian J. 2010, 5, 2199-2208
15. Chen, C.; Kehr, G.; Fröhlich, R.; Erker, G. J. Am. Chem. Soc. 2010, 132, 13594-13595
16. Stephan, D. W.; Erker, G. Angew. Chem. 2010, 122, 50-81
17. Angew. Chem., Int. Ed. 2010, 49, 46-76.
18. Knüppel, S.; Fröhlich, R.; Erker, G. J. Organomet. Chem. 1999, 586, 218-222
19. Knüppel, S.; Fröhlich, R.; Erker, G. J. Organomet. Chem. 2000, 595, 307-312
20. See for a comparison: Knüppel, S.; Erker, G.; Fröhlich, R. Angew. Chem. 1999, 111, 2048-2051
21. Angew. Chem., Int. Ed. 1999, 38, 1923-1926.
22. Bai, S.-D.; Wie, X.-H.; Guo, J.-P.; Liu, D.-S.; Zhou, Z.-Y. Angew. Chem. 1999, 111, 2051-2054
23. Angew. Chem., Int. Ed. 1999, 38, 1926-1928.
24. Knüppel, S.; Wang, C.; Kehr, G.; Fröhlich, R.; Erker, G. J. Organomet. Chem. 2005, 690, 14-32
25. Liptau, P.; Knüppel, S.; Kehr, G.; Kataeva, O.; Fröhlich, R.; Erker, G. J. Organomet. Chem. 2001, 637-639, 621-630
26. Liptau, P.; Seki, T.; Kehr, G.; Abele, A.; Fröhlich, R.; Erker, G.; Grimme, S. Organometallics 2003, 22, 2226-2232
27. Tebben, L.; Kehr, G.; Fröhlich, R.; Erker, G. Eur. J. Inorg. Chem. 2008, 2654-2658
28. Chen, C.; Fröhlich, R.; Kehr, G.; Erker, G. Organometallics 2008, 27, 3248-3253
29. Tainturier, G.; Chhor y Sok, K.; Gautheron, B. C. R. Acad. Sci. Paris, Ser. C 1973, 1269-1270
30. Chhor y Sok, K.; Tainturier, G.; Gautheron, B. Tetrahedron Lett. 1974, 25, 2207-2208
31. Chhor y Sok, K.; Tainturier, K.; Gautheron, B. J. Organomet. Chem. 1977, 132, 173-189
32. Tebben, L.; Kehr, G.; Fröhlich, R.; Erker, G. Synthesis 2004, 1971-1976
33. Liptau, P.; Neumann, M.; Erker, G.; Kehr, G.; Fröhlich, R.; Grimme, S. Organometallics 2994, 23, 21-25
34. Nilewski, C.; Neumann, M.; Tebben, L.; Fröhlich, R.; Kehr, G.; Erker, G. Synthesis 2006, 13, 2191-2200
35. Marquarding, D.; Klusacek, H.; Gokel, G.; Hoffmann, P.; Ugi, I. J. Am. Chem. Soc. 1970, 92, 5389
36. Gokel, G.; Marquarding, D.; Ugi, I. J. Org. Chem. 1972, 37, 3052
37. Hayashi, T.; Mise, T.; Fukushima, M.; Kagotani, M.; Nagashima, N.; Hamada, Y.; Matsumoto, A.; Kawakami, S.; Konishi, M.; Yamamoto, K.; Kumada, M. Bull. Chem. Soc. Jpn. 1980, 53, 1138
38. Ganter, C.; Wagner, T. Chem. Ber. 1995, 128, 1157
39. Nöth, H.; Wrackmeyer, B. in NMR Basic Principles and Progress, Vol. 14; Springer: Berlin, 1978; p 461.
40. Wrackmeyer, B.; Köster, R. in Methods in Organic Chemistry; Houben-Weyl, 1984; Vol. 13, p 406.
41. Wrackmeyer, B. Annu. Rep. NMR Spectrosc. 1988, 20, 61
42. Beringhelli, T.; Donghi, D.; Maggioni, D.; D'Alfonso, G. Coord. Chem. Rev. 2008, 252, 2292-2313, and references therein
43. Piers, W. E. Adv. Organomet. Chem. 2004, 52, 1-76
44. Widhalm, M.; Nettekoven, U.; Mereiter, K. Tetrahedron: Asymmetry 1999, 10, 4369-4391
45. Tebben, L.; Bussmann, K.; Hegemann, M.; Kehr, G.; Fröhlich, R.; Erker, G. Organometallics 2008, 17, 4269-4272
46. For similar synthesis on ferrocene see: Maishal, T. K.; Mondal, B.; Puranik, V. G.; Wadgaonkar, P. P.; Lahiri, G. K.; Sarkar, A. J. Organomet. Chem. 2005, 690, 1019-1027
47. Spies, P.; Erker, G.; Kehr, G.; Bergander, K.; Fröhlich, R.; Grimme, S.; Stephan, D. W. Chem. Commun. 2007, 5072-5074
48. Spies, P.; Kehr, G.; Bergander, K.; Wibbeling, B.; Fröhlich, R.; Erker, G. Dalton Trans. 2009, 1534-1541
49. Spies, P.; Schwendemann, S.; Lange, S.; Kehr, G.; Fröhlich, R.; Erker, G. Angew. Chem. 2008, 120, 7654-7657
50. Angew. Chem., Int. Ed. 2008, 47, 7543-7546.
51. Mömming, C. M.; Otten, E.; Kehr, G.; Fröhlich, R.; Grimme, S.; Stephan, D. W.; Erker, G. Angew. Chem. 2009, 121, 6770-6773
52. Angew. Chem., Int. Ed. 2009, 48, 6643-6646.
53. For similar syntheses on ferrocene see: Debroy, P.; Nakar, D.; Roy, S. Inorg. Chim. Acta 2006, 1215-1221
54. Reich, H. J.; Chow, F.; Shah, S. K. J. Am. Chem. Soc. 1979, 101, 6648-6656
55. Brown, H. C.; Dhar, R. K.; Ganesan, K.; Singaram, B. J. Org. Chem. 1992, 57, 499-504
56. Stirling, A.; Hamza, A.; Rokob, T. A.; Papai, I. Chem. Commun. 2008, 3148-3150
57. Guo, Y.; Li, S. Eur. J. Inorg. Chem. 2008, 2501-2505
58. For other theoretical frustrated Lewis pair studies see e.g.: Rokob, T. A.; Hamza, A.; Stirling, A.; Papai, I. J. Am. Chem. Soc. 2009, 131, 2029-2036
59. Rokob, T. A.; Hamza, A.; Papai, I. J. Am. Chem. Soc. 2009, 131, 10701-10710
60. Guo, Y.; He, X.; Li, Z.; Zou, Z. Inorg. Chem. 2010, 49, 3419-3423
61. Grimme, S.; Kruse, H.; Goerigk, L.; Erker, G. Angew. Chem. 2010, 122, 1444-1447
62. Angew. Chem., Int. Ed. 2010, 49, 1402-1405.
63. See for a comparison: Ulrich, M.; Seto, K.; Lough, A. J.; Stephan, D. W. Chem. Commun. 2008, 2335-2337
64. Liptau, P.; Knüppel, S.; Kehr, G.; Kataeva, O.; Fröhlich, R.; Erker, G. J. Organomet. Chem. 2001, 637-639, 621-630
65. Lambert, J. B.; So, J.-H. J. Org. Chem. 1991, 56, 5962-5964
66. Massey, A. G.; Park, A. J. in Organometallic Syntheses; King, R. B.; Eisch, J. J., Eds.; Elsevier: New York, 1986; Vol. 3, pp 461-462.
67. Massey, A. G.; Park, A. J. J. Organomet. Chem. 1964, 2, 245-250