Different reactivities of Alkoxy- And Thiocarbene complexes of fischer-type: Formation of (N-Enamino)ethoxycarbene complexes and Quinolines, respectively

Organometallics

Volumn 29, Issue 4, 2010, Pages 801-805

  Karataş, Betül ^a,b   Aumann, Rudolf ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b AHI EVRAN UNIVERSITY   (Turkey)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDOYL CHLORIDE;

CHLORINE COMPOUNDS; CHROMIUM; CHROMIUM COMPOUNDS; TUNGSTEN;

TUNGSTEN COMPOUNDS;

EID: 76849089001     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om900807s     Document Type: Article

References (46)

1. (a) Negishi, E. In Comrehensive Organic Synthesis; Trost, B. M., Fleming I., Eds.; Pergamon: Oxford, 1991; Vol. 5, p 1163;
2. (b) Corey, E. J.; Cheng, X. The Logic of Chemical Synthesis; Wiley-Interscience: New York, 1989.
3. (a) Frühauf, H.-W. Chem. Rev. 1997, 97, 523-596.
4. (b) Lautens, M; Klute, W.; Tarn, W. Chem. Rev. 1996, 96, 49-92.
5. For selected recent reviews, see: (a) Santamaria, J. Curr. Org. Chem. 2009, 13, 31-46.
6. (b) Sierra, M. A.; Fernandez, I.; Cossio, F. P. Chem. Commun. 2008, 4671-4682.
7. (c) Herndon, J. W. Coord. Chem. Rev. 2009, 253,86-179.
8. (d) Waters, M. L.; Wulff, W. D. Org. React. 2008, 70, 121-623.
9. (e) Kagoshima, H.; Fuchibe, K.; Akiyama, T. Chem. Rec 2007, 7, 104-114.
10. (f) Sierra, M. A.; Gomez-Gallego, M.; Martinez-Alvarez, R. Chem.-Eur. J. 2007, 13, 736-744.
11. (g) Barluenga, J.; Martinez, S. ARKIVOC 2006, 129-147.
12. (a) Capriati, V.; Florio, S.; Luisi, R.; Perna, F. M.; Barluenga, J. J. Org. Chem. 2005, 70, 5852-5858.
13. (b) Florio, S.; Perna, F. M.; Luisi, R.; Barluenga, J.; Rodriguez, F.; Fananas, F. J. J. Org. Chem. 2004, 69, 5480-5482.
14. (a) Minatti, A; Dötz, K. H. Top. Organomet. Chem. 2004, 13, 123-156.
15. (b) Sola, M.; Duran, M.; Torrent, M. Catal. Met. Complexes 2002,25, 269-287.
16. (a) Hegedus, L. S. Top. Organomet. Chem, 2004, 13, 157-201.
17. (b) Hegedus, L. S. Tetrahedron 1997, 53, 4105-4127.
18. Selected recent references on reactions of Fischer carbene complexes with NH/C=N bond-containing compounds: (a) Nitsche, F.; Aumann, R.; Fröhlich, R. J. Organomet. Chem. 2007, 692, 2971-2989.
19. (b) Barluenga, J.; Garcia-Rodriguez, J.; Martinez, S.; Suarez-Sobrino, A. L.; Tomas, M. Chem-Eur. J. 2006, 12, 3201-3210.
20. (c) Zheng, Z.; Yu, Z.; Luo, N.; Han, X. J. Org. Chem. 2006, 71, 9695-9700.
21. (d) Gu, K.; Chen, J.; Zheng, Z.; Wu, S.; Wu, X.; Han, X.; Yu, Z. Polyhedron 2005, 24, 173-180.
22. (e) Chen, J.; Yu, Z.; Zheng, Z.; Gu, K.; Wu, S.; Zeng, F.; Tan, W; Wu, X.; Xiao, W. Organometallics 2005, 24, 302-308.
23. Kouznetsov, V. V.; Vargas Méndez, L. Y.; Meléndez Gómez, C. M. Curr. Org. Chem. 2005, 9, 141-161.
24. Quinolines from Fischer carbene complexes: (a) Barluenga, J.; Fananas-Mastral, M.; Aznar, F.; Valdes, C. Angew. Chem., Int. Ed. 2008, 47, 6594-6597.
25. (b) Jana, G. P.; Ghorai, B. K. Tetrahedron 2007, 63, 12015-12025.
26. (c) Wulff, W. D.; Glen, A. P. Tetrahedron Lett. 1997, 38, 5587-5590.
27. Manske, R. H. F.; Kulka, M. Org. React. 1953, 7, 59-98.
28. Bergstrom, F. W. Chem. Rev. 1944, 35, 77-211.
29. Cheng, C.-C.; Yan, S.-J. Org. React. 1982, 28, 37-201.
30. Jones, G. In The Chemistry of Heterocyclic Compounds; Weissberger, A., Taylor, E. C., Eds.; John Wiley and Sons: Chichester, 1977; Vol. 32, Part I, pp 93-318.
31. Reitsema, R. H. Chem. Rev. 1948, 43,43-68.
32. (a) Katritzky, A. R.; Rachwal, S.; Rachwal, B. Tetrahedron 1996, 52,15031-15070.
33. (b) Kouznetsov, V.; Palma, A.; Ewert, C.; Varlamov, A. J. Heterocycl. Chem. 1998, 35, 761-785.
34. (a) Karatas, B.; Hyla-Kryspin, I.; Aumann, R. Organometallics 2007, 26, 4983-4996.
35. (b) Aumann, R.; Fu, X.; Vogt, D.; Fröhlich, R.; Kataeva, O. Organometallics 2002, 21, 2736-2742.
36. (c) Unaldi, S.; Aumann, R.; Fröhlich, R. Chem.-Eur. J. 2003, 9, 3300-3309.
37. Recent review concerning the Povarov reaction: Kouznetsov, V. V. Tetrahedron 2009, 65, 2721-2750.
38. (a) Dobbelaar, P. H.; Marzabadi, C. H. Tetrahedron Lett. 2010, 51,201-204.
39. (b) Melendez Gomez, C. M.; Kouznetsov, V. V.; Sortino, M. A.; Alvarez, S. L.; Zacchino, S. A. Bioorg. Med. Chem. 2008, 16, 7908-7920.
40. (c) Geng, X.; Li, S.; Bian, X.; Xie, Z.; Wang, C. ARKIVOC2008, 14, 50-57.
41. (a) Liu, H.; Dagousset, G.; Masson, G.; Retailleau, P.; Zhu, J. J. Am, Chem. Soc. 2009, 131, 4598-4599.
42. (b) Akiyama, T; Morita, H.; Fuchibe, K. J. Am. Chem. Soc. 2006, 128, 13070-13071.
43. (a) Demaude, T.; Knerr, L.; Pasau, P. P. J. Comb. Chem. 2004, 6, 768-775.
44. (b) Makioka, Y.; Shindo, T.; Taniguchi, Y.; Takaki, K.; Fujiwara, Y. Synthesis 1995, 801-804
45. Cho, C. S.; Kim, B. T.; Choi, H. J.; Shim, S. C. Tetrahedron 2003, 59, 7997-8002.
46. (a) Nerdel, F.; Weyerstahl, P.; Dahl, R. Liebigs Ann. Chem. 1968, 716, 127-134.