P-stereogenic ferrocene-based (Trifluoromethyl)phosphanes: Synthesis, structure, coordination properties and catalysis

European Journal of Organic Chemistry

Volumn , Issue 1, 2011, Pages 78-87

  Sondenecker, Aline ^a   Cvengroš, Ján ^a   Aardoom, Raphael ^a   Togni, Antonio ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

Asymmetric catalysis; Chiral auxiliaries; Electrophilic trifluoromethylation; Ferrocene; Ligand design; Phosphanes

Indexed keywords

EID: 78650820568     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201001162     Document Type: Article

References (39)

1. Ferrocenes: Homogeneous Catalysis, Organic Synthesis Materials Science (Eds.:, A. Togni, T. Hayashi), VCH, Weinheim, 1995.
2. Ferrocenes: Ligands, Materials and Biomolecules (Eds.:, P. Stepnicka), Wiley, Chichester, 2008.
3. R. G. Arrayás, J. Adrio, J. C. Carretero, Angew. Chem. 2006, 118, 7836-7878
4. Angew. Chem. Int. Ed. 2006, 45, 7674-7715.
5. A. Togni, C. Breutel, A. Schnyder, F. Spindler, H. Landert, A. Tijiani, J. Am. Chem. Soc. 1994, 116, 4062-4066.
6. A. Togni, Chimia 1996, 50, 86-93.
7. H.-U. Blaser, B. Pugin, F. Spindler, M. Thommen, Acc. Chem. Res. 2007, 40, 1240-1250.
8. R. N. Haszeldine, B. O. West, J. Chem. Soc. 1956, 3631-3637.
9. W. R. Cullen, Can. J. Chem. 1960, 38, 439-444.
10. M. A. A. Beg, H. C. Clark, Can. J. Chem. 1961, 39, 564-570.
11. M. A. A. Beg, H. C. Clark, Can. J. Chem. 1962, 40, 283-288.
12. I. Tworowska, W. Dabkowski, J. Michalski, Angew. Chem. 2001, 113, 2982-2984
13. Angew. Chem. Int. Ed. 2001, 40, 2898-2900.
14. P. Panne, D. Naumann, B. Hoge, J. Fluorine Chem. 2001, 112, 283-286.
15. R. P. Singh, A. Vij, R. L. Kirchmeier, J. M. Shreeve, Inorg. Chem. 2000, 39, 375-377.
16. M. B. Murphy-Jolly, L. C. Lewis, A. J. M. Caffyn, Chem. Commun. 2005, 4479-4480.
17. T. Umemoto, S. Ishihara, J. Am. Chem. Soc. 1993, 115, 2156-2164.
18. E. J. Velazco, A. J. M. Caffyn, Organometallics 2008, 27, 2402-2404.
19. P. Eisenberger, S. Gischig, A. Togni, Chem. Eur. J. 2006, 12, 2579-2586.
20. P. Eisenberger, I. Kieltsch, N. Armanino, A. Togni, Chem. Commun. 2008, 1575-1577.
21. 3-organoiodine compounds as electrophilic trifluoromethylating reagents, see
22. I. Kieltsch, P. Eisenberger, A. Togni, Angew. Chem. 2007, 119, 768-771
23. Angew. Chem. Int. Ed. 2007, 46, 754-757.
24. K. Stanek, R. Koller, A. Togni, J. Org. Chem. 2008, 73, 7678-7685.
25. R. Koller, K. Stanek, D. Stolz, R. Aardoom, K. Niedermann, A. Togni, Angew. Chem. 2009, 121, 4396-4400
26. Angew. Chem. Int. Ed. 2009, 48, 4332-4336.
27. R. Koller, Q. Huchet, P. Battaglia, J. M. Welch, A. Togni, Chem. Commun. 2009, 5993-5995.
28. S. Fantasia, J. M. Welch, A. Togni, J. Org. Chem. 2010, 75, 1779-1782.
29. N. Armanino, R. Koller, A. Togni, Organometallics 2010, 29, 1771-1777.
30. F. Pass, E. Steininger, H. Schindlbauer, Monatsh. Chem. 1959, 90, 792-798.
31. D. Marquarding, H. Klusacek, G. Gokel, P. Hoffmann, I. Ugi, J. Am. Chem. Soc. 1970, 92, 5389-5393.
32. S.-I. Fukuzawa, D. Tsuchiya, K. Sasamoto, K. Hirano, M. Ohtaguchi, Eur. J. Org. Chem. 2000, 2877-2883.
33. M. Steurer, K. Tiedl, Y. Wang, W. Weissensteiner, Chem. Commun. 2005, 4929-4931.
34. A. Rauk, L. C. Allen, K. Mislow, Angew. Chem. Int. Ed. Engl. 1970, 9, 400-414.
35. For a general discussion of conformational aspects of ferrocenyl ligands, see: Metallocenes (Eds.:, A. Togni, R. L. Haltermann), Wiley, New York, 1998, chapter 11.
36. For an alternative synthesis of the bis(phosphane) 3, see:, J. Cabou, J. Brocard, L. Pélinski, Tetrahedron Lett. 2005, 46, 1185-1188.
37. H. A. Bent, Chem. Rev. 1961, 61, 275-311.
38. D. Drew, J. R. Doyle, Inorg. Synth. 1990, 28, 346.
39. J. L. Herde, J. C. Lambert, C. V. Senoff, M. A. Cushing, Inorg. Synth. 1974, 15, 18.