Bulky-alkyl-substituted bis(trifluorovinyl)ferrocenes: Redox-autocatalytic formation of fluorinated ferrocenophanes

Organometallics

Volumn 31, Issue 4, 2012, Pages 1500-1510

  Roemer, Max ^a   Heinrich, Darina ^a   Kang, Youn Kyung ^b   Chung, Young Keun ^c   Lentz, Dieter ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b Sangmyung University   (South Korea)

^c Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUPS; CARBONYL FUNCTION; COUPLING REACTION; CYCLIC ETHER; CYCLIZATIONS; DILITHIATION; ELECTRON-DONATING; ELECTRONWITHDRAWING; EXCHANGE REACTION; FERROCENES; FERROCENOPHANES; FLUORINE ATOMS; FLUOROUS; INTRAMOLECULAR SUBSTITUTIONS; IRON CENTERS; REDOX BEHAVIOR; TERT-BUTYL GROUP; TRI-N-BUTYLTIN; X-RAY SINGLE-CRYSTAL DIFFRACTION;

CHEMICAL REACTIONS; CHLORINE COMPOUNDS; CYCLIC VOLTAMMETRY; FLUORINE; IODINE; IRON COMPOUNDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TIN;

ORGANOMETALLICS;

EID: 84857548808     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om2009765     Document Type: Article

References (57)

1. Hughes, R. P. J. Fluorine Chem. 2010, 131, 1059-1070
2. Grushin, V. V. Acc. Chem. Res. 2010, 43, 160-171
3. Chalykh, G. P.; Sokolova, E. B.; Chernysheva, T. I. Zh. Obshch. Khim. 1970, 40, 2337-2338
4. Bruce, M. I.; Melvin, M. J. J. Chem. Soc. 1969, 2107-2112
5. Deck, P. A.; Jackson, W. F. Organometallics 1996, 15, 5287-5291
6. Blanchard, M. D.; Hughes, R. P.; Concolino, T. E.; Rheingold, A. L. Chem. Mater. 2000, 12, 1604-1610
7. Deck, P. A.; Lane, M. L.; Montgomery, J. L.; Slebodnick, C.; Fronczek, F. R. Organometallics 2000, 19, 1013-1024
8. Thornberry, M. P.; Slebodnick, C.; Deck, P. A.; Fronczek, F. R. Organometallics 2000, 19, 5352-5369
9. Gassman, P. G.; Winter, C. H. J. Am. Chem. Soc. 1986, 108, 4228-4229
10. Akiyama, T.; Kato, K.; Kajitani, M.; Sakaguchi, Y.; Nakamura, J.; Hayashi, H.; Sugimori, A. G. Bull. Chem. Soc. Jpn. 1988, 61, 3531-3537
11. Čermák, J.; Žádný, J.; Krupková, A.; Lopatová, K.; Vlachová, A.; Thi, T. H. N.; Šauliová, J.; Sýkora, J.; Císařová, I. J. Organomet. Chem. 2007, 692, 1557-1570
12. Čermák, J.; Krupková, A.; Auerová, K.; Zamrzla, M.; Thi, T. H. N.; Vojtíšek, P.; Císař ová, I. J. Organomet. Chem. 2010, 695, 375-381
13. Bříza, T.; Kvíčala, J.; Paleta, O.; Čermák, J. Tetrahedron 2002, 58, 3847-3854
14. Herrera, V.; De Rege, P. J. F.; Horváth, I. T.; Husebo, T. L.; Hughes, R. P. Inorg. Chem. Commun. 1998, 1, 197-199
15. Hughes, R. P.; Trujillo, H. A. Organometallics 1996, 15, 286-294
16. Hughes, R. P.; Husebo, T. L.; Rheingold, A. L.; Liable-Sands, L. M.; Yap, G. P. A. Organometallics 1997, 16, 5-7
17. Hughes, R. P.; Maddock, S. M.; Guzei, I. A.; Liable-Sands, L. M.; Rheingold, A. L. J. Am. Chem. Soc. 2001, 123, 3279-3288
18. Hazafy, D.; Sobociková, M.; Štěpnička, P.; Ludvik, J.; Kotora, M. J. Fluorine Chem. 2003, 124, 177-181
19. King, A.; Okukado, N.; Negishi, E.-I. J. Chem. Soc., Chem. Commun. 1977, 683-684
20. Negishi, E.-I.; Liu, F. Palladium- or Nickel-catalyzed Cross-coupling with Organometals Containing Zinc, Magnesium, Aluminum, and Zirconium. In Metal-catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; pp 1-47.
21. Dinh, L. V.; Gladysz, J. A. Chem.-Eur. J. 2005, 11, 7211-7222
22. Roemer, M.; Schmiel, P.; Lentz, D. Organometallics 2011, 30, 2063-2066
23. Roemer, M.; Lentz, D. Eur. J. Inorg. Chem. 2008, 4875-4878
24. Roemer, M.; Lentz, D. Chem. Commun. 2011, 47, 7239-7241
25. Roemer, M.; Kang, Y. K.; Chung, Y. K.; Lentz, D. Chem.-Eur. J. 2011. Manuscript in preparation.
26. Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704-4734
27. Akkerman, F. A.; Kickbusch, R.; Lentz, D. Chem.-Asian J. 2008, 3, 719-731
28. Raghavanpillai, A.; Burton, D. J. J. Org. Chem. 2004, 69, 7083-7091
29. Roemer, M.; Kang, Y. K.; Chung, Y. K.; Lentz, D. Manuscript in preparation.
30. Masson, G.; Lough, A. J.; Manners, I. Macromolecules 2008, 41, 539-547
31. Masson, G.; Beyer, P.; Cyr, P. W.; Lough, A. J.; Manners, I. Macromolecules 2006, 39, 3720-3730
32. Compton, D. L.; Rauchfuss., T. B. Organometallics 1994, 13, 4367-4376
33. Freiesleben, W. Angew. Chem., Int. Ed. Engl. 1963, 2, 396-397
34. Leigh, T. J. Chem. Soc. 1964, 3294-3302
35. Knox, G. R.; Pauson, P. L. J. Am. Chem. Soc. 1961, 902, 4610-4615
36. Hine, J.; Knight, D. B. J. Org. Chem. 1970, 35, 3946-3949
37. Knight, D. B.; Hartless, R. L.; Jarvis, D. A. J. Org. Chem. 1972, 37, 688-692
38. Tomori, H.; Fox, J. M.; Buchwald, S. L. J. Org. Chem. 2000, 65, 5334-5341
39. Schlummer, B.; Scholz, U. Adv. Synth. Catal. 2004, 346, 1599-1626
40. Mauger, C. C.; Mignani, G. A. Aldrichimica Acta 2006, 39, 17-24
41. Nesmeyanov, A. N.; Kritskaya, I.; Antipina, T. V. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1962, 11, 1685-1690
42. Sato, H. Hyperfine Interact. 1990, 57, 2089-2094
43. Gleixner, R. M.; Joly, K. M.; Tremayne, M. J.; Kariuki, B. M.; Male, L.; Coe, D. M.; Cox, L. R. Chem.-Eur. J. 2010, 16, 5769-5777
44. Hisatome, M.; Yamakawa, K. J. Chem. Soc., Chem. Commun. 1973, 199-200
45. Hisatome, M.; Minagawa, S.; Yamakawa, K. J. Organomet. Chem. 1973, 55, 82-84
46. Hisatome, M.; Minagawa, S.; Chimura, K.; Hashimoto, H.; Yamakawa, K. J. Organomet. Chem. 1973, 145, 225-239
47. Hisatome, M.; Hashiama, T.; Yamakawa, K. Tetrahedron Lett. 1978, 3759-3762
48. Horspool, W. M.; Sutherland, R. G.; Sutton, J. R. Can. J. Chem. 1970, 48, 3542-3544
49. Horspool, W.; Stanley, P.; Sutherland, R.; Thomson, B. J. Chem. Soc. C 1971, 1365-1369
50. Härter, P.; Latzel, K.; Spiegler, M.; Herdtweck, E. Polyhedron 1998, 17, 1141-1148
51. LeSuer, R.; Geiger, W. Angew. Chem., Int. Ed. 2000, 39, 248-250
52. Camire, N.; Mueller-Westerhoff, U. T.; Geiger, W. E. J. Organomet. Chem. 2001, 637-639, 823-826
53. Bruña, S.; González-Vadillo, A. M.; Nieto, D.; Pastor, C.; Cuadrado, I. Organometallics 2010, 29, 2796-2807
54. Gericke, H. J.; Barnard, N. I.; Erasmus, E.; Swarts, J. C.; Cook, M. J.; Aquino, M. A. S. Inorg. Chim. Acta 2010, 363, 2222-2232
55. Harrowven, D. C.; Guy, I. L. Chem. Commun. 2004, 1968-1969
56. SHELX-97 (release 97-2): Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112-122
57. ORTEP-3 for Windows: Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565