Triferrocenylsilane and unexpected formation of diferrocenyl(3,3- dimethylbutyl)silane via cleavage and trapping of a tetrahydrofuran fragment. Redox chemistry and synthesis of (Fc)3Si-Co(CO)4 through oxidative addition of the si-h bond

Journal of Organometallic Chemistry

Volumn 751, Issue , 2014, Pages 769-780

  Bruña, Sonia ^a   Perles, Josefina ^a   Nieto, Daniel ^a   González Vadillo, Ana Ma ^a   Cuadrado, Isabel ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

Electrochemistry; Ferrocene; Hydrosilanes; Silicon

Indexed keywords

CARBON DIOXIDE; ELECTROCHEMISTRY; ELECTROLYTES; ETHYLENE; ORGANOMETALLICS; REDOX REACTIONS; SILICON; SINGLE CRYSTALS; X RAY DIFFRACTION;

ELECTROCHEMICAL STUDIES; ELECTRONIC INTERACTIONS; FERROCENES; HYDROSILANES; ORGANOLITHIUM SPECIES; SINGLE-CRYSTAL X-RAY DIFFRACTION STUDIES; SUPPORTING ELECTROLYTE; TETRAHYDROFURAN SOLVENTS;

ORGANIC SOLVENTS;

EID: 84893788321     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2013.07.052     Document Type: Article

References (98)

1. (a) P. Stèpnicka (Ed.), Ferrocenes. Ligands Materials and Biomolecules, John Wiley & Sons Ltd, Chichester, 2008;
2. A. Togni, T. Hayashi (Eds.), Ferrocenes: Homogeneous Catalysis-organic Synthesis-materials Science, VCH Verlagsgesellschaft, Weinheim, 1995.
3. A. Togni, R.L. Halterman (Eds.), Metallocenes. Synthesis, Reactivity, Applications, Wiley-VCH, 1998.
4. (Ed.) I. Manners (Ed.), Synthetic Metal-containing Polymers, Wiley-VCH, Weinheim, Germany, 2004;
5. A.S. Abd-El-Aziz, I. Manners (Eds.), Frontiers in Transition Metal-containing Polymers, Wiley-Interscience, Hoboken, NJ, 2007.
6. A.E. Kaifer, M. Gómez-Kaifer (Eds.), Supramolecular Electrochemistry, Wiley- VCH, Weinheim: Germany, 1999.
7. P. Zanello, C. Nervi, F. Fabrizi de Biani (Eds.), Inorganic Electrochemistry. Theory, Practice and Application, second ed., Royal Society of Chemistry, Cambridge, 2012 (Chapter 5).
8. S. Barlow, D. O'Hare, Chem. Rev. 97 (1997) 637-670.
9. (a) Recent examples of compounds with electronically communicated ferrocenes assembled through carbon-based spacers: (a) J.M. Speck, D. Schaarschmidt, H. Lang, Organometallics 31 (2012) 1975-1982;
10. J.M. Speck, R. Claus, A. Hildebrandt, T. Rüffer, E. Erasmus, L. van As, J.C. Swarts, H. Lang, Organometallics 31 (2012) 6373-6380;
11. U. Pfaff, A. Hildebrandt, D. Schaarschmidt, T. Rüffer, T. Hahn, J. Kortus, H. Lang, Organometallics 31 (2012) 6761-6771;
12. Y. Li, M. Josowicz, L.M. Tolbert, J. Am. Chem. Soc. 132 (2010) 10374-10382;
13. A. Donoli, A. Bisello, R. Cardena, C. Prinzivalli, S. Santi, Organometallics 32 (2013) 1029-1036;
14. Y.-K. Lim, S. Wallace, J.C. Bollinger, X. Chen, D. Lee, Inorg. Chem. 46 (2007) 1694-1703;
15. P.V. Solntsev, S.V. Dudkin, J.R. Sabin, V.N. Nemykin, Organometallics 30 (2011) 3037-3046;
16. H. Huesmann, C. Förster, D. Siebler, T. Gasi, K. Heinze, Organometallics 31 (2012) 413-427.
17. Representative examples of compounds with multiple ferrocenyl groups bridged by p-block elements (E). E = Si: (a) D.E. Herbert, J.B. Gilroy, W.Y. Chan, L. Chabanne, A. Staubitz, A.J. Lough, I. Manners, J. Am. Chem. Soc. 131 (2009) 14958-14968;
18. R. Rulkens, A.J. Lough, I. Manners, S.R. Lovelace, C. Grant, W.E. Geiger, J. Am. Chem. Soc. 118 (1996) 12683-12695;
19. V.V. Dementiev, F. Cervantes-Lee, L. Parkanyi, H. Sharma, K.H. Pannell, M.T. Nguyen, A.F. Diaz, Organometallics 12 (1993) 1983-1987;
20. M.T. Nguyen, A.F. Diaz, V.V. Dementiev, K.H. Pannell, Chem. Mater. 5 (1993) 1389-1394;
21. K.H. Pannell, V.V. Dementiev, H. Li, F. Cervantes-Lee, M.T. Nguyen, A.F. Diaz, Organometallics 13 (1994) 3644-3650;
22. B. Alonso, E. Ramírez, M. Zamora, C.M. Casado, I. Cuadrado, J. Organomet. Chem. 637-639 (2001) 642-652 (E = P);
23. G.F. Barrière, R.U. Kirss, W.E. Geiger, Organometallics 24 (2005) 48-52;
24. A.R. Seibert, M.F. Cain, D.S. Glueck, C. Nataro, J. Organomet. Chem. 696 (2011) 2259-2262 (E = B);
25. L. Kaufmann, J.-M. Breunig, H. Vitze, F. Schoedel, I. Nowik, M. Pichlmaier, M. Bolte, H.-W. Lerner, R.F. Winter, R.H. Herber, M. Wagner, Dalton Trans. (2009) 2940-2950 (E = S);
26. P.F. Brandt, T.B. Rauchfuss, J. Am. Chem. Soc. 114 (1992) 1926;
27. V.C. Gibson, N.J. Long, R.J. Long, A.J.P. White, C.K. Williams, D.J. Williams, E. Grigiotti, P. Zanello, Organometallics 23 (2004) 957-967 (E = N);
28. (l) J. Alvarez, T. Ren, A.E. Kaifer, Organometallics 20 (2001) 3543-3549.
29. W.E. Geiger, Organometallics 26 (2007) 5738-5765.
30. T. López, A. Campero, J. Organomet. Chem. 378 (1989) 91-98.
31. (a) M. Herberhold, M. Ellinger, U. Thewalt, F. Stollmaier, Angew. Chem. Int. Ed. 21 (1982) 74-75;
32. W.E. Britton, R. Kashyap, M. El-Hashash, M. El-Kady, M. Herberhold, Organometallics 5 (1986) 1029-1031.
33. G.P. Sollott, E. Howard, J. Org. Chem. 27 (1962) 4034-4040.
34. J.R. Garabatos Perera, R. Wartchow, H. Butenschön, J. Organomet. Chem. 689 (2004) 3541-3549.
35. M.J. MacLachlan, J. Zheng, K. Thieme, A.J. Lough, I. Manners, C. Mordas, R. LeSuer, W.E. Geiger, L.-M. Liable-Sands, A.L. Rheingold, Polyhedron 19 (2000) 275-289.
36. I. Cuadrado, Organometallic Silicon-containing Dendrimers and their Electrochemical Applications, in: P. Dvornic, M.J. Owen (Eds.), Silicon-containing Dendritic Polymers, Springer, Berlin, 2009, pp. 141-196.
37. (a) S. Bruña, A.M. González-Vadillo, D. Nieto, C.J. Pastor, I. Cuadrado, Macromolecules 45 (2012) 781-793;
38. M. Zamora, S. Bruña, B. Alonso, I. Cuadrado, Macromolecules 44 (2011) 7994-8007;
39. M. Zamora, B. Alonso, C. Pastor, I. Cuadrado, Organometallics 26 (2007) 5153-5164;
40. (d) B. García, C.M. Casado, I. Cuadrado, B. Alonso, M. Morán, J. Losada, Organometallics 18 (1999) 2349-2356;
41. B. Alonso, I. Cuadrado, M. Morán, J. Losada, J. Chem. Soc. Chem. Commun. (1994) 2575-2576;
42. B. Alonso, M. Morán, C.M. Casado, F. Lobete, J. Losada, I. Cuadrado, Chem. Mater. 7 (1995) 1440-1443;
43. I. Cuadrado, C.M. Casado, B. Alonso, M. Morán, J. Losada, V. Belsky, J. Am. Chem. Soc. 119 (1997) 7613-7614.
44. S. Bruña, A.M. González-Vadillo, D. Nieto, C.J. Pastor, I. Cuadrado, Organometallics 29 (2010) 2796-2807.
45. S. Bruña, D. Nieto, A.M. González-Vadillo, J. Perles, I. Cuadrado, Organometallics 31 (2012) 3248-3258.
46. B. Marciniec (Ed.), Hydrosilylation. A Comprehensive Review on Recent Advances, Springer Science, New York, 2009.
47. L.I. Kopylova, N.D. Ivanova, M.G. Voronkov, Zh. Obshch. Khim. 55 (1985) 1649-1651.
48. (a) R. Arias-Ugarte, H.K. Sharma, A.J. Metta-Magaña, K.H. Pannell, Organometallics 30 (2011) 6506-6509;
49. H.K. Sharma, K.H. Pannell, Angew. Chem. Int. Ed. 48 (2009) 7052-7054;
50. R. Arias-Ugarte, H.K. Sharma, A.L.C. Morris, K.H. Pannell, J. Am. Chem. Soc. 134 (2012) 848-851.
51. J.Y. Corey, Chem. Rev. 111 (2011) 863-1071.
52. T.D. Tilley, in: S. Patai, Z. Rappoport (Eds.), The Chemistry of Organic Silicon Compounds, John Wiley and Sons, New York, 1989, pp. 1415-1477. Part 2, (Chapter 24).
53. (a) D. Guillaneux, H.B. Kagan, J. Org. Chem. 60 (1995) 2502-2505;
54. B. Bildstein, M. Malaun, H. Kopacka, K. Wurst, M. Mitterböck, K.- H. Ongania, G. Opromolla, P. Zanello, Organometallics 18 (1999) 4325-4336;
55. R. Sander, U.T. Mueller-Westherhoff, J. Organomet. Chem. 512 (1996) 219-224.
56. (a) M.D. Rausch, D.J. Ciappenelli, J. Organomet. Chem. 10 (1967) 127-136;
57. J.J. Bishop, A. Davison, M.L. Katcher, D.W. Lichtenberg, R.E. Merrill, J.C. Smart, J. Organomet. Chem. 27 (1971) 241-249;
58. R.F. Kovar, M.D. Rausch, H. Rosenberg, Organomet. Chem. Syn. 1 (1970/1971) 173;
59. D.A. Rider, K.A. Cavicchi, N.K. Power-Billard, T.P. Russell, I. Manners, Macromolecules 38 (2005) 6931-6938.
60. Y. Ni, I. Manners, J.B. Sheridan, R.T. Oakley, J. Chem. Educ. 75 (1998) 766-768.
61. (a) S.I. Goldberg, D.W. Mayo, Chem. Ind. 671 (1959);
62. S.I. Goldberg, D.W. Mayo, H. Rosenberg, M.D. Rausch, J. Org. Chem. 24 (1959) 824-826;
63. A.C. Macdonald, J. Trotter, Acta. Crystallogr. 17 (1964) 872-877.
64. J. Clayden, S.A. Yasin, New J. Chem. 26 (2002) 191-192.
65. R.E. Mulvey, V.L. Blair, W. Clegg, A.R. Kennedy, J. Klett, L. Russo, Nat. Chem. 2 (2010) 588-591.
66. M. Schlosser (Ed.), Organometallics in Synthesis; a Manual, second ed., Wiley, Chichester, 2002.
67. J. Clayden (Ed.), Organolithiums: Selectivity for Synthesis, Elsevier Science/Pergamon, 2002.
68. W. Malisch, M. Vögler, D. Schumacher, M. Nieger, Organometallics 21 (2002) 2891-2897 (See also references therein).
69. A.J. Chalk, J.F. Harrod, J. Am. Chem. Soc. 87 (1965) 1133-1135.
70. (a) J. Greene, M.D. Curtis, Inorg. Chem. 17 (1978) 2324-2326;
71. J.S. McIndoe, B.K. Nicholson, J. Organomet. Chem. 577 (1999) 181-188;
72. S. Bourg, B. Boury, F.H. Carré, R.J.P. Corriu, Organometallics 17 (1998) 167-172;
73. S. Bourg, B. Boury, F.H. Carré, R.J.P. Corriu, Organometallics 16 (1997) 3097-3099;
74. M. Zirngast, C. Marschner, J. Baumgartner, Organometallics 25 (2006) 4897-4908.
75. I. Cuadrado, M. Morán, A. Moya, C.M. Casado, M. Barranco, B. Alonso, Inorg. Chim. Acta 251 (1996) 5-7.
76. A. Berenbaum, F. Jäkle, A.J. Lough, I. Manners, Organometallics 20 (2001) 834-843.
77. S. Kotani, T. Tanizawa, K. Shiina, K. Sonogashira, Chem. Lett. (1990) 1889-1892.
78. A search in the literature has revealed us that there is a previous example in which a Si-OH-containing octasilsesquioxane was obtained from the corresponding Si-H-functionalized precursor, from a reaction in which Co2(CO)8 was present as catalysts M.A. Said, H.W. Roesky, C. Rennekamp, M. Andruh, H.-G. Schmidt, M. Noltemeyer, Angew. Chem. Int. Ed. 38 (1999) 661-664.
79. G.P. Sollott, W.R. Peterson, J. Am. Chem. Soc. 89 (1967) 6783-6784.
80. D. Astruc (Ed.), Electron-transfer and Radical Processes in Transition Metal Chemistry, VCH, New York, 1995 (Chapter 1).
81. W.E. Geiger, F. Barrière, Acc. Chem. Res. 43 (2010) 1030-1039.
82. When [n-Bu4N][PF6] is used as the supporting electrolyte in the low polarity dichloromethane solvent, the strong ion pairing between the positively charged electrogenerated ferrocenium species and the [PF6]- anion of the electrolyte, leave little or any electrostatic effect. See: A.K. Diallo, C. Absalon, J. Ruiz, D. Astruc J. Am. Chem. Soc. 133 (2011) 629-641.
83. D.A. Foucher, C.H. Honeyman, J.M. Nelson, B.Z. Tang, I. Manners, Angew. Chem. Int. Ed. Engl. 32 (1993) 1709-1711.
84. (a) For leading references on the dependence of DE1/2 values in organometallic compounds on different experimental conditions, such as solvents, electrolytes and temperatures see: (a) F. Barrière, W.E. Geiger, J. Am. Chem. Soc. 128 (2006) 3980-3989;
85. A. Nadafy, T.T. Chin, W.E. Geiger, Organometallics 25 (2006) 1654-1663;
86. F. Barrière, N. Camire, W.E. Geiger, U.T. Mueller-Westerhoff, R. Sanders, J. Am. Chem. Soc. 124 (2002) 7262-7263;
87. R.J. LeSuer, W.E. Geiger, Angew. Chem. Int. Ed. 39 (2000) 248-250.
88. A. Nadafy, W.E. Geiger, Organometallics 27 (2008) 5624-5631.
89. J. Osteryoung, J.J. O'Dea, in: A.J. Bard (Ed.), Electroanalytical Chemistry, vol. 14, Marcel Dekker, Inc., New York, 1986.
90. D.E. Richardson, H. Taube, Inorg. Chem. 20 (1981) 1278-1285.
91. Both the E1/2 and the splitting ΔE1/2 values are strongly dependent on the solvent and supporting electrolyte anion employed. See Refs. [41,44].
92. M.B. Robin, P. Day, Adv. Inorg. Chem. Radiochem. 10 (1967) 247-422.
93. R.J. LeSuer, C. Buttolph, W.E. Geiger, Anal. Chem. 76 (2004) 6395-6401.
94. SAINT+NT Version 6.04; SAX Area-detector Integration Program, Bruker Analytical X-ray Instruments, Madison, WI, 1997-2001.
95. G.M. Sheldrick, SADABS Version 2.03, Program for Empirical Absorption Correction, University of Göttingen, Germany, 1997-2001.
96. Bruker AXS SHELXTL Version 6.10, Structure Determination Package, Bruker Analytical X-ray Instruments, Madison, WI, 2000.
97. G.M. Sheldrick, Acta Crystallogr. A. 46 (1990) 467.
98. G.M. Sheldrick, SHELXL97, Program for Crystal Structure Refinement, 1997. Germany.