Ferrocenes with perfluorinated side chains and ferrocenophanes with fluorinated handles

Chemistry - A European Journal

Volumn 18, Issue 11, 2012, Pages 3371-3389

  Roemer, Max ^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

C C coupling; cycloaddition; ferrocene; fluorine; homogeneous catalysis

Indexed keywords

AUTOCATALYTIC; BUILDING BLOCKES; C-C COUPLING; COUPLING REACTION; CYCLOPENTADIENYL LIGANDS; FERROCENES; FERROCENOPHANES; FLUORINATED SIDE CHAINS; FLUORINE ATOMS; FLUORINE SUBSTITUENTS; HOMOGENEOUS CATALYSIS; IRON CENTERS; NUCLEOPHILIC SUBSTITUTIONS; OXIDIZING AGENTS; REDOX PROPERTY; SIDE-CHAINS; SINGLE CRYSTAL X-RAY DIFFRACTION; STANNANE; SYNTHETIC TRANSFORMATIONS;

CHLORINE COMPOUNDS; CYCLIC VOLTAMMETRY; CYCLOADDITION; FLUORINE; IRON COMPOUNDS; ORGANOMETALLICS; REACTION KINETICS; SILICA; X RAY DIFFRACTION;

SILANES;

EID: 84857887705     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201102508     Document Type: Article

References (85)

1. T. J. Kealy, P. L. Pauson, Nature 1951, 168, 1039-1040.
2. S. A. Miller, J. A. Tebboth, J. F. Tremaine, J. Chem. Soc. 1952, 632-635.
3. P. Štěpnička, Ferrocenes: Ligands, Materials and Biomolecules, Wiley, Chichester, 2008
4. A. Togni, T. Hayashi, Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Material Science, Wiley-VCH, Weinheim, 1995
5. A. Togni, in Metallocenes: Synthesis, Reactivity, Applications (Eds.:, A. Togni, R. L. Halterman,), Wiley-VCH, Weinheim, 1998, pp. 685-721
6. I. Manners, in Metallocenes: Synthesis, Reactivity, Applications (Eds.:, A. Togni, R. L. Halterman,), Wiley-VCH, Weinheim, 1998, pp. 723-772.
7. A special issue has been dedicated to ferrocene and its derivatives: J. Organomet. Chem. 2001, 637, 1-875
8. I. R. Butler, in Comprehensive Organometallic Chemistry III, Vol. 6 (Eds.:, R. H. Crabtree, D. M. P. Mingos,), Elsevier, Amsterdam, 2007, pp. 185-220
9. R. J. Meyer, E. H. E. Pietsch, A. Kotowski, M. Becke-Göhring, K. C. Buschbeck, Gmelins Handbuch der Anorganischen Chemie, Vol. 8, Springer, Berlin, 1974.
10. U. T. Mueller-Westerhoff, Angew. Chem. 1986, 98, 700-716
11. Angew. Chem. Int. Ed. Engl. 1986, 25, 702-717
12. R. W. Heo, T. R. Lee, J. Organomet. Chem. 1999, 578, 31-42
13. D. E. Herbert, U. F. J. Mayer, I. Manners, Angew. Chem. 2007, 119, 5152-5173
14. Angew. Chem. Int. Ed. 2007, 46, 5060-5081.
15. R. P. Hughes, J. Fluorine Chem. 2010, 131, 1059-1070
16. V. V. Grushin, Acc. Chem. Res. 2010, 43, 160-171.
17. A. M. Thayer, Chem. Eng. News 2006, 84, 15-24.
18. M. I. Bruce, M. J. Melvin, J. Chem. Soc. 1969, 2107-2112
19. P. A. Deck, W. F. Jackson, Organometallics 1996, 15, 5287-5291
20. M. D. Blanchard, R. P. Hughes, T. E. Concolino, A. L. Rheingold, Chem. Mater. 2000, 12, 1604-1610
21. P. A. Deck, M. L. Lane, J. L. Montgomery, C. Slebodnick, F. R. Fronczek, Organometallics 2000, 19, 1013-1024
22. M. P. Thornberry, C. Slebodnick, P. A. Deck, F. R. Fronczek, Organometallics 2000, 19, 5352-5369.
23. P. G. Gassman, C. H. Winter, J. Am. Chem. Soc. 1986, 108, 4228-4229.
24. T. Akiyama, K. Kato, M. Kajitani, Y. Sakaguchi, J. Nakamura, H. Hayashi, A. G. Sugimori, Bull. Chem. Soc. Jpn. 1988, 61, 3531-3537.
25. G. P. Chalykh, E. B. Sokolova, T. I. Chernysheva, Zh. Obshch. Khim. 1970, 40, 2337-2338.
26. L. V. Dinh, J. A. Gladysz, Chem. Eur. J. 2005, 11, 7211-7222.
27. J. Čermák, J. Žádný, A. Krupková, K. Lopatová, A. Vlachová, T. H. N. Thi, J. Šauliová, J. Sýkora, I. Císařová, J. Organomet. Chem. 2007, 692, 1557-1570
28. J. Čermák, A. Krupková, K. Auerová, M. Zamrzla, T. H. N. Thi, P. Vojtíšek, I. Císař ová, J. Organomet. Chem. 2010, 695, 375-381
29. J. Kvíčala, T. Bříza, O. Paleta, K. Auerová, J. Čermák, Tetrahedron 2002, 58, 3847-3854.
30. V. Herrera, P. J. F. De Rege, I. T. Horváth, T. L. Husebo, R. P. Hughes, Inorg. Chem. Commun. 1998, 1, 197-199
31. R. P. Hughes, H. A. Trujillo, Organometallics 1996, 15, 286-294
32. R. P. Hughes, T. L. Husebo, A. L. Rheingold, L. M. Liable-Sands, G. P. A. Yap, Organometallics 1997, 16, 5-7
33. R. P. Hughes, S. M. Maddock, I. A. Guzei, L. M. Liable-Sands, A. L. Rheingold, J. Am. Chem. Soc. 2001, 123, 3279-3288.
34. D. Hazafy, M. Sobociková, P. Štěpnička, J. Ludvik, M. Kotora, J. Fluorine Chem. 2003, 124, 177-181.
35. G. S. Smith, S. K. Patra, L. Vanderark, S. Saithong, J. P. H. Charmant, I. Manners, Macromol. Chem. Phys. 2010, 211, 303-312.
36. M. Roemer, D. Lentz, Eur. J. Inorg. Chem. 2008, 4875-4878.
37. M. Roemer, P. Schmiel, D. Lentz, Organometallics 2011, 30, 2063-2066.
38. M. Roemer, D. Lentz, Chem. Commun. 2011, 47, 7239-7241.
39. F. Babudri, A. Cardone, L. De Cola, G. Farinola, G. Kottas, C. Martinelli, F. Naso, Synthesis 2008, 1580-1588.
40. P. Espinet, A. M. Echavarren, Angew. Chem. 2004, 116, 4808-4839
41. Angew. Chem. Int. Ed. 2004, 43, 4704-4734.
42. C. C. Mauger, G. A. Mignani, Aldrichimica Acta 2006, 39, 17-24.
43. A. King, N. Okukado, E.-I. Negishi, J. Chem. Soc. Chem. Commun. 1977, 683-684
44. E.-I. Negishi, F. Liu, in Metal-Catalyzed Cross-Coupling Reactions (Eds.:, F. Diederich, P. J. Stang,), Wiley-VCH, Weinheim, 1998, pp. 1-47.
45. V. A. Nefedov, Zh. Obshch. Khim. 1966, 36, 1954
46. M. D. Rausch, D. Ciappenelli, J. Organomet. Chem. 1967, 10, 127-136.
47. F. Rebière, O. Riant, L. Ricard, H. B. Kagan, Angew. Chem. 1993, 105, 644-646
48. Angew. Chem. Int. Ed. Engl. 1993, 32, 568-570
49. D. H. Hua, M. Lagneau, Y. Chen, P. M. Robben, G. Clapham, G.; P. D. Robinson, J. Org. Chem. 1996, 61, 4508-4509
50. P. D. Robinson, J. Org. Chem. 1996, 61, 4508-4509
51. O. G. Mancheño, J. Priego, S. Cabrera, R. G. Arrayás, T. Llamas, J. C. Carretero, J. Org. Chem. 2003, 68, 3679-3686
52. C. Fan, B. Ferber, H. Kagan, O. Lafon, P. Lesot, Tetrahedron: Asymmetry 2008, 19, 2666-2677.
53. D. Lentz, M. Mujkic, D. Lentz, Eur. J. Inorg. Chem. 2008, 2967-2970
54. M. Balbo-Block, C. Bartel, D. Lentz, D. Preugschat, Chem. Eur. J. 2001, 7, 881
55. C. Bartel, P. Botschwina, H. Bürger, A. Guarnieri, Î. Heyl, A. Huckauf, D. Lentz, T. Merzliak, El B. Mkadmi, Angew. Chem. 1998, 110, 3036-3040
56. Angew. Chem. Int. Ed. 1998, 37, 2879-2882.
57. N. Nagahora, A. Yuasa, T. Sasamori, N. Tokitoh, Acta Crystallogr. Sect. E 2007, 63, m 2702.
58. L. J. Farrugia, C. Evans, D. Lentz, M. Roemer, J. Am. Chem. Soc. 2009, 131, 1251-1268.
59. B. E. Smart, in Chemistry of Organic Fluorine Compounds II (Eds.:, M. Hudlicky, A. E. Pavlath,), American Chemical Society, Washington DC, 1995, pp. 767-796.
60. D. Lentz, F. Nowak, D. Preugschat, M. Wasgindt, Angew. Chem. 1993, 105, 1547-1549
61. Angew. Chem. Int. Ed. Engl. 1993, 32, 1456-1458.
62. B. K. Spraul, S. Suresh, J. Jin, D. W. Smith, J. Am. Chem. Soc. 2006, 128, 7055-7064
63. B. K. Spraul, S. Suresh, S. Glaser, D. Perahia, J. Ballato, D. W. Smith, J. Am. Chem. Soc. 2004, 126, 12772-12773
64. A. R. Neilson, S. M. Buddy, J. M. Ballato, D. W. Smith Jr, Macromolecules 2007, 40, 9378-9383.
65. N. Mifsud, V. Mellon, J. Jin, C. M. Topping, L. Echegoyen, D. W. Smith Jr, Polym. Int. 2007, 56, 1142-1146.
66. R. M. Gleixner, K. M. Joly, M. Tremayne, B. M. Kariuki, L. Male, D. M. Coe, L. R. Cox, Chem. Eur. J. 2010, 16, 5769-5777.
67. A. N. Nesmeyanov, I. Kritskaya, T. V. Antipina, Bull. Acad. Sci. USSR Div. Chem. Sci. 1962, 11, 1685-1690
68. H. Sato, Hyperfine Interact. 1990, 57, 2089-2094.
69. J. W. Emsley, J. Feeney, L. H. Sutcliff, High Resolution Nuclear Magnetic Resonance Spectroscopy, Pergamon Press, Oxford, 1966.
70. R. LeSuer, W. Geiger, Angew. Chem. 2000, 112, 254-256
71. Angew. Chem. Int. Ed. 2000, 39, 248-250
72. N. Camire, U. T. Mueller-Westerhoff, W. E. Geiger, J. Organomet. Chem. 2001, 637-639, 823-826
73. S. Bruna, A. M. Gonza'lez-Vadillo, D. Nieto, D.; C. Pastor, I. Cuadrado, Organometallics 2010, 29, 2796-2807
74. H. J. Gericke, N. I. Barnard, E. Erasmus, J. C. Swarts, M. J. Cook, M. A. S. Aquino, Inorg. Chim. Acta 2010, 363, 2222-2232.
75. L. Cuffe, R. D. A. Hudson, J. F. Gallagher, S. Jennings, C. J. McAdam, R. B. T. Connelly, A. R. Manning, B. H. Robinson, J. Simpson, Organometallics 2005, 24, 2051-2060.
76. G. Masson, P. Beyer, P. W. Cyr, A. J. Lough, I. Manners, Macromolecules 2006, 39, 3720-3730.
77. P. F. Brandt, T. B. Rauchfuss, J. Am. Chem. Soc. 1992, 114, 1926-1927.
78. D. L. Compton, T. B. Rauchfuss, Organometallics 1994, 13, 4367-4376.
79. D. Guillaneux, H. B. Kagan, J. Org. Chem. 1995, 60, 2502-2505.
80. M. E. Wright, Organometallics 1990, 9, 853-856.
81. F. A. Akkerman, R. Kickbusch, D. Lentz, Chem. Asian J. 2008, 3, 719-731.
82. A. Raghavanpillai, D. J. Burton, J. Org. Chem. 2004, 69, 7083-7091.
83. D. C. Harrowven, I. L. Guy, Chem. Commun. 2004, 1968-1969.
84. SHELX-97 (release 97-2), G. M. Sheldrick, University of Göttingen, Germany, 1998.
85. ORTEP-3 for Windows:, L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.