Synthesis of arylferrocenylketones

Arkivoc

Volumn 2005, Issue 6, 2005, Pages 250-265

  Rodríguez Cendejas, Cristina G ^a   Liebeskind, Lanny S ^b   Peña Cabrera, Eduardo ^a  

^a UNIVERSITY OF GUANAJUATO   (Mexico)

^b EMORY UNIVERSITY   (United States)

Author keywords

Boronic acids; Copper TC; Ferrocenylketones; Liebeskind Srogl cross coupling reaction; Palladium; Thiolesters

Indexed keywords

EID: 23044482257     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (40)

1. E-mail L. S. L. chemLL1@emory.edu
2. th Anniversary of the Discovery of Ferrocene J. Organomet. Chem. 2001, 637-639.
3. Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Material Science; Togni, A., Hayashi, T., Eds.; VCH: New York, 1995.
4. (a) Top, S.; Vessières, A.; Leclerq, G.; Quivy, J.; Tang, J.; Vaisserman, J.; Huché, M.; Jaouen, G. Chem. Eur. J. 2003, 9, 5223.
5. (b) Top, S.; Vessières, A.; Cabestaing, C.; Laïos, I.; Leclerq, G.; Provot, C.; Jaouen, G. J. Organomet. Chem. 2001, 637, 500.
6. (a) Carollo, L.; Curulli, A.; Floris, B. Appl. Organomet. Chem. 2003, 17, 589
7. (b) Sarhan, A. E-W.; Nouchi, Y.; Izumi, T. Tetrahedron 2003, 59, 6353.
8. Denifl, P.; Hradsky, A.; Bildstein, B.; Wurst, K. J. Organomet. Chem. 1996, 523, 79.
9. Miller, E. J.; Weigelt, C. A.; Serth, J. A.; Rusyid, R.; Brenner, J.; Luck, L. A.; Godlewski, M. J. J. Organomet. Chem. 1992, 440, 91.
10. (a) Wittenberg, R.; Srögl, J.; Egi, M.; Liebeskind, L. S. Org. Lett. 2003, 5(17), 3033
11. (b) Liebeskind, L. S.; Srögl, J. J. Am. Chem. Soc. 2000, 122, 11260
12. (c) Yu, Y.; Liebeskind, L. S. J. Org. Chem. 2004, 69 (10), 3554.
13. For other examples of cross-couplings of sulfur-containing substrates see: (a) Aguilar-Aguilar, A.; Peña-Cabrera, E.; Liebeskind, L. S. ARKIVOC 2004, (i), 156
14. (b) Kusturin, C.; Liebeskind, L. S.; Rahman, H.; Sample, K.; Schweitzer, B.; Srogl, J.; Neumann, W. L. Org. Lett. 2003, 5(23), 4349
15. (c) Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2001, 3(1), 91
16. (d) Savarin, C.; Liebeskind, L. S. Org. Lett 2001, 3(14), 2149
17. (e) Srogl, J.; Liebeskind, L. S. Org. Lett. 2002, 4(6), 979
18. (f) Kusturin, C.; Liebeskind, L. S.; Neumann, W. L. Org. Lett. 2002, 4(6), 983
19. (g) Liebeskind, L. S.; Srogl, J.; Savarin, C.; Polanco, C. Pure Appl. Chem. 2002, 74(1), 115
20. (h) Egi, M.; Liebeskind, L. S. Org. Lett. 2003, 5(6), 801
21. (i) Alphonse, F.-A.; Suzenet, F.; Keromnes, A.; Lebret, B.; Guillaumet, G. Org. Lett. 2003, 5, 803.
22. (a) Suzuki, A. J. Organomet. Chem. 1999, 576, 147
23. (b) Stanforth, S. P. Tetrahedron 1998, 54, 263
24. (c) Tyrrell, E.; Brookes, P. Synthesis 2004, 469.
25. (a) Tokuyama, H.; Yokoshima, S.; Yamashita, T.; Fukuyama, T. Tetrahedron Lett. 1998, 39, 3189
26. (b) Neises, B.; Steglich, W. Angew. Chem., Int. Ed. 1978, 17(7), 522.
27. Miyazaki, T.; Han-ya, Y.; Tokuyama, H.; Fukuyama, T. Synlett 2004, 477.
28. Taber, D. F.; Petty, E. H.; Raman, K. J. Am. Chem. Soc. 1985, 107,196.
29. 1,1'-Ferrocenedicarboxylic acid is commercially available.
30. For the generation of 1,1'-bislithioferrocene see McCulloch, Brubaker Jr.; C. H. Organometallics 1984, 3, 1707.
31. (a) Miyazaki, T.; Han-ya, Y.; Tokuyama, H.; Fukuyama, T. Synlett 2004, 477
32. (b) Tokuyama, H.; Miyazaki, T.; Yokoshima, S.; Fukuyama, T. Synlett 2004, 477
33. (c) Tokuyama, H.; Yokoshima, S.; Yamashita, T.; Fukuyama, T. Tetrahedron Lett. 1998, 39, 3189.
34. Zhang, S.; Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1997, 62, 2312.
35. 2TMEDA is highly pyrophoric.
36. Skrydstrup, Hansen, S. G.; Laursen, B.; Rasmussen, B. S.; Larsen, J.; Sorensen, H. S.; T.; Amatore, C.; Jutand, A. Organometallics 2002, 21, 5243.
37. Meth-Cohn, O.; Walshe, N. D. A.; Bin Din, L. Tetrahedron Lett., 1979, 49, 4783.
38. Voguel, M.; Rosenberg, H.; Rausch, M. J. Org. Chem. 1957, 22, 903.
39. Carollo, L.; Curulli, A.; Floris, B. Appl. Organomet. Chem. 2003, 17, 589.
40. Sarhan, A.; Nouchi, Y.; Izumi, T. Tetrahedron. 2003, 6353.