Metal-free frustrated lewis pair catalyzed 1,4-hydrogenation of conjugated metallocene dienamines

Organometallics

Volumn 29, Issue 5, 2010, Pages 1067-1069

  Schwendemann, Sina ^a   Tumay, Tülay Ash ^a   Axenov, Kirill V ^a   Peuser, Ilona ^a   Kehr, Gerald ^a   Fröhlich, Roland ^a   Erker, Gerhard ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMBIENT TEMPERATURES; CATALYTIC CONDITIONS; DIHYDROGEN; FERROCENES; METALLOCENES; SELECTIVE HYDROGENATION; ZIRCONOCENES;

IRON COMPOUNDS; ORGANOMETALLICS; ZIRCONIUM COMPOUNDS;

HYDROGENATION;

EID: 77749267618     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om900963p     Document Type: Article

References (48)

1. (a) Welch, G. C.; San Juan, R. R.; Masuda, J. D.; Stephan, D. W. Science 2006, 314, 1124-1126.
2. (b) McCahill, J. S. J.; Welch, G. C.; Stephan, D. W. Angew. Chem. 2007, 119, 5056-5059;
3. Angew. Chem., Int. Ed. 2007, 46, 4968-4971.
4. (c) Welch, G. C.; Stephan, D. W. J. Am. Chem. Soc. 2007, 129, 1880-1881.
5. (d) Welch, G. C.; Cabrera, L.; Chase, P. A.; Hollink, E.; Masuda, J. D.; Wei, P.; Stephan, D. W. Dalton Trans. 2007, 3407-3414.
6. (e) Sumerin, V.; Schulz, F.; Nieger, M.; Leskelä, M.; Repo, T.; Rieger, B. Angew. Chem. 2008, 120, 6090-6092;
7. Angew. Chem., Int. Ed. 2008, 47, 6001-6003.
8. (f) Sumerin, V.; Schulz, F.; Atsumi, M.; Wang, C.; Nieger, M.; Leskelä, M.; Repo, T.; Pyykkö, P.; Rieger, B. J. Am. Chem. Soc. 2008, 130, 14117-14119.
9. (g) Chase, P. A.; Stephan, D. W. Angew. Chem. 2008, 120, 7543-7547;
10. Angew. Chem., Int. Ed. 2008, 47, 7433-7437.
11. (h) Holschumacher, D.; Bannenberg, T.; Hrib, C. G.; Jones, P. G.; Tamm, M. Angew. Chem. 2008, 120, 7538-7542;
12. Angew. Chem., Int. Ed. 2008, 47, 7428-7432.
13. (i) Huber, D. P.; Kehr, G.; Bergander, K.; Fröhlich, R.; Erker, G.; Tanino, S.; Ohki, Y.; Tatsumi, K Organometallics 2008, 27, 5279-5284.
14. (j) Geier, S. J.; Gilbert, T. M.; Stephan, D. W. J. Am. Chem. Soc. 2008, 130, 12632-12633.
15. (k) Ullrich, M.; Lough, A. J.; Stephan, D. W. J. Am. Chem. Soc. 2009, 131, 52-53.
16. (l) Ramos, A.; Lough, A. J.; Stephan, D. W. Chem. Commun. 2009, 1118-1120. Reviews:
17. (m) Stephan, D. W. Org. Biomol. Chem. 2008, 6, 1535-1539.
18. (n) Kenward, A. L.; Piers, W. E. Angew. Chem. 2008, 120, 38-42;
19. Angew. Chem., Int. Ed. 2008, 47, 38-41.
20. (o) Stephan, D. W.; Erker, G. Angew. Chem. 2010, 122, 50-81;
21. Angew. Chem., Int. Ed. 2010, 49, 46-76.
22. (a) Chase, P. A.; Jurca, T.; Stephan, D. W. Chem. Commun. 2008, 1701-1703.
23. (b) Chen, D.; Klankermayer, J. Chem. Commun. 2008, 2130-2131.
24. (a) Spies, P.; Erker, G.; Kehr, G.; Bergander, K.; Fröhlich, R.; Grimme, S.; Stephan, D. W. Chem. Commun. 2007, 5072-5074.
25. (b) Spies, P.; Kehr, G.; Bergander, K.; Wibbeling, B.; Fröhlich, R.; Erker, G. Dalton Trans. 2009, 1534-1541.
26. Spies, P.; Schwendemann, S.; Lange, S.; Kehr, G.; Fröhlich, R.; Erker, G. Angew. Chem. 2008, 120, 7654-7657;
27. Angew. Chem., Int. Ed. 2008, 47, 7543-7546.
28. Wang, H.; Fröhlich, R.; Kehr, G.; Erker, G. Chem. Commun. 2008, 5966-5968.
29. Axenov, K. V.; Kehr, G.; Fröhlich, R.; Erker, G. J. Am. Chem. Soc. 2009, 131, 3454-3455.
30. (a) Knüppel, S.; Fröhlich, R.; Erker, G. J. Organomet. Chem. 1999, 586, 218-222.
31. (b) Knüppel, S.; Fröhlich, R.; Erker, G. J. Organomet. Chem. 2000, 595, 308-312.
32. (c) Liptau, P.; Knüppel, S.; Kehr, G.; Kataeva, O.; Fröhlich, R.; Erker, G. J. Organomet. Chem. 2001, 637-639, 621-630.
33. (a) Liptau, P.; Tebben, L.; Kehr, G.; Wibbeling, B.; Fröhlich, R.; Erker, G. Eur. J. Inorg. Chem. 2003, 3590-3600.
34. (b) Liptau, P.; Carmona, D.; Oro, L. A.; Lahoz, F. J.; Kehr, G.; Erker, G. Eur. J. Inorg. Chem. 2004, 4586-4590.
35. (a) Liptau, P.; Tebben, L.; Kehr, G.; Fröhlich, R.; Erker, G.; Hollmann, F.; Rieger, B. Eur. J. Org. Chem. 2005, 1909-1918.
36. (b) Liptau, P.; Seki, T.; Kehr, G.; Abele, A.; Fröhlich, R.; Erker, G.; Grimme, S. Organometallics 2003, 22, 2226-2232.
37. It is likely that the small amount of the fully saturated hydrogenation product 2 is a slowly formed follow-up product of 3 and is potentially formed from 3 via an isomerization pathway. For details see the Supporting Information.
38. (a) Knüppel, S.; Wang, C.; Kehr, G.; Fröhlich, R.; Erker, G. J. Organomet. Chem. 2005, 690, 14-32 and references cited therein.
39. (b) Knüppel, S.; Erker, G.; Fröhlich, R. Angew. Chem. 1999, 111, 2048-2051;
40. Angew. Chem., Int. Ed. 1999, 38, 1923-1926.
41. (c) Bai, S.-D.; Wei, X.-H.; Guo, J.-P.; Liu, D.-S.; Zhou, Z.-Y. Angew. Chem. 1999, 111, 2051-2054;
42. Angew. Chem., Int. Ed. 1999, 38, 1926-1928.
43. - salts see: (a) Parks, D. J.; Blackwell, J. M.; Piers, W. E. J. Org. Chem. 2000, 65, 3090-3098.
44. (b) Rubin, M.; Schwier, T.; Gevorgyan, V. J. Org. Chem. 2002, 67, 1936-1940.
45. (c) Schwier, T.; Gevorgyan, V. Org. Lett. 2005, 7, 5191-5194.
46. (d) Di Saverio, A.; Focante, F.; Camurati, I.; Resconi, L.; Beringhelli, T.; D'Alfonso, G.; Donghi, D.; Maggioni, D.; Mercandelli, P.; Sironi, A. W. Inorg. Chem. 2005, 44, 5030-5041.
47. Liptau, P.; Neumann, M.; Erker, G.; Kehr, G.; Fröhlich, R.; Grimme, S. Organometallies 2004, 23, 21-25.
48. 3; for details see the Supporting Information.