Electrochemistry of 1,1′-bis(2,4-dialkylphosphetanyl)ferrocene and 1,1′-bis(2,5-dialkylphospholanyl)ferrocene ligands: Free phosphines, metal complexes, and chalcogenides

Inorganic Chemistry

Volumn 49, Issue 20, 2010, Pages 9718-9727

  Mandell, Chelsea L ^a   Kleinbach, Shannon S ^a,c   Dougherty, William G ^b   Kassel, W Scott ^b   Nataro, Chip ^a  

^a LAFAYETTE COLLEGE   (United States)

^b VILLANOVA UNIVERSITY   (United States)

^c Heraeus Circuit Materials Division   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 78549276897     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic1016164     Document Type: Article

References (85)

1. Sollot, G. P.; Snead, S.; Portnoy, S.; Peterson, W. R., Jr.; Mertwoy, H. E. Chem. Abstr. 1965, 63, 18147b.
2. (a) Gan, K.-S.; Hor, T. S. A. 1, 1′-Bis (diphenylphosphino) ferrocene - Coordination Chemistry, Organic Synthesis and Catalysis. In Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science; Togni, A., Hayashi, T., Eds.; VCH: Weinheim, Germany, 1995; pp 3-104.
3. (b) Hayashi, T. Asymmetric Catalysis with Chiral Ferrocenylphosphine Ligands. In Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science; Togni, A., Hayashi, T., Eds.; VCH: Weinheim, Germany, 1995; pp 105-142.
4. (c) Chien, S. W.; Hor, T. S. A. The Coordination and Homogeneous Catalytic Chemistry of 1, 1′-Bis (diphenylphosphino) ferrocene and its Chalcogenide Derivatives. In Ferrocenes: Ligands, Materials and Biomolecules; Štěpnička, P., Ed.; John Wiley & Sons Ltd.: West Sussex, England, 2008; pp 33-116.
5. (d) Colacot, T. J.; Parisel, S. Synthesis, Coordination Chemistry and Catalytic Use of dppf Analogs. In Ferrocenes: Ligands, Materials and Biomolecules; Štěpnička, P., Ed.; John Wiley & Sons Ltd.: West Sussex, England, 2008; pp 117-140.
6. (e) Štěpnička, P. 1′-Functionalized Ferrocene Phosphines: Synthesis, Coordination Chemistry and Catalytic Applications. In Ferrocenes: Ligands, Materials and Biomolecules; Štěpnička, P., Ed.; John Wiley & Sons Ltd.: West Sussex, England, 2008; pp 177-204.
7. (f) Blaser, H.-U.; Chen, W.; Camponovo, F; Togni, A. Chiral 1, 2-Disubstituted Ferrocene Diphosphines for Asymmetric Catalysis. In Ferrocenes: Ligands, Materials and Biomolecules; Štěpnička, P., Ed.; John Wiley & Sons Ltd.: West Sussex, England, 2008; pp 205-236.
8. (a) You, J.; Drexler, H.-J.; Zhang, S.; Fischer, C.; Heller, D. Angew. Chem., Int. Ed. 2003, 42, 913.
9. (b) Berens, U.; Burk, M. J.; Gerlach, A.; Hems, W. Angew. Chem., Int. Ed. 2009, 39, 1981.
10. (a) Heller, D.; Drexler, H.-J.; You, J.; Baumann, W.; Drauz, K.; Krimmer, H.-P.; Börner, A. Chem.-Eur. J. 2002, 8, 5196.
11. (b) Allwardt, A.; Holzmüller-Laue, S.; Wendler, C.; Stoll, N. Catal. Today 2008, 137, 11.
12. (c) Lennon, I. C.; Ramsden, J. A.; Brear, C. J.; Broady, S. D.; Muir, J. C. Tetrahedron Lett. 2007, 48, 4623.
13. (d) Alame, M.; Pestre, N.; de Bellefon, C. Adv. Synth. Catal. 2008, 350, 898.
14. (a) Cobley, C. J.; Henschke, J. P. Adv. Synth. Catal. 2003, 345, 195.
15. (b) Qin, L.; Prashad, M.; Hu, B.; Prasad, K.; Repič, O.; Blacklock, T. J.; Kwong, F. Y.; Kok, S. H. L.; Lee, H. W.; Chan, A. S. C. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 16787.
16. (c) Schäffner, B.; Andrushko, V.; Holz, J.; Verevkin, S. P.; Börner, A. ChemSusChem 2008, 1, 934.
17. Marinetti, A.; Labrue, F.; Genêt, J.-P. Synlett. 1999, 1975.
18. Marinetti, A.; Labrue, F.; Pons, B.; Jus, S.; Ricard, L.; Genêt, J.-P. Eur. J. Inorg. Chem. 2003, 2583.
19. Myers, M.; Connor, E. F.; Glauser, T.; Möck, A.; Nyce, G.; Hedrick, J. L. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 844.
20. (a) Korff, C; Helmchen, G. Chem. Commun. 2004, 530.
21. (b) Yamamoto, Y; Takada, S.; Miyaura, N.; Iyama, T.; Tachikawa, H. Organometallics 2009, 28, 152.
22. Pican, S.; Gaumont, A.-C. Chem. Commun. 2005, 2393.
23. Assié, M.; Legros, J.-Y.; Fiaud, J.-C. Tetrahedron: Asymmetry 2005, 16, 1183.
24. (a) Fleury-Brégeot, N.; Jean, L.; Retailleau, P.; Marinetti, A. Tetrahedron 2007, 63, 11920.
25. (b) Jean, L.; Marinetti, A. Tetrahedron Lett. 2006, 47, 2141.
26. Brissy, D.; Skander, M.; Retailleau, P.; Frison, G.; Marinetti, A. Organometallics 2009, 28, 140.
27. Anderson, B. J.; Glueck, D. S.; DiPasquale, A. G.; Rheingold, A. L. Organometallics 2008, 27, 4992.
28. Chan, V. S.; Bergman, R. G.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 15122.
29. Burk, M. J.; Gross, M. F. Tetrahedron Lett. 1994, 35, 9363.
30. Fox, M. E.; Jackson, M.; Lennon, I. C; Klosin, J.; Abboud, K. A. J. Org. Chem. 2008, 73, 775.
31. Axtell, A. T.; Klosin, J.; Whiteker, G. T.; Cobley, C. J.; Fox, M. E.; Jackson, M.; Abboud, K. A. Organometallics 2009, 28, 2993.
32. Cobley, C. J.; Lennon, I. C.; Praquin, C.; Zanotti-Gerosa, A.; Appell, R. B.; Goralski, C. T.; Sutterer, A. C. Org. Process Res. Dev. 2003, 7, 407.
33. Brunker, T. J.; Blank, N. F.; Moncarz, J. R.; Scriban, C.; Anderson, B. J.; Glueck, D. S.; Zakharov, L. N.; Golen, J. A.; Sommer, R. D.; Incarvito, C. D.; Rheingold, A. L. Organometallics 2005, 24, 2730.
34. Axtell, A. T.; Cobley, C. J.; Klosin, J.; Whiteker, G. T.; Zanotti-Gerosa, A.; Abboud, K. A. Angew. Chem., Int. Ed. 2005, 44, 5834.
35. Appleby, I.; Boulton, L. T.; Cobley, C. J.; Hill, C.; Hughes, M. L.; de Koning, P. D.; Lennon, I. C.; Praquin, C.; Ramsden, J. A.; Samuel, H. J.; Willis, N. Org. Lett. 2005, 7, 1931.
36. Blank, N. F.; Moncarz, J. R.; Brunker, T. J.; Scriban, C.; Anderson, B. J.; Amir, O.; Glueck, D. S.; Zakharov, L. N.; Golen, J. A.; Incarvito, C. D.; Rheingold, A. L. J. Am. Chem. Soc. 2007, 129, 6847.
37. (a) Nataro, C.; Campbell, A. N.; Ferguson, M. A.; Incarvito, C. D.; Rheingold, A. L. J. Organomet. Chem. 2003, 673, 47.
38. (b) Ong, J. H. L.; Nataro, C.; Golen, J. A.; Rheingold, A. L. Organometallics 2003, 22, 5027.
39. (c) Blanco, F. N.; Hagopian, L. E.; McNamara, W. R.; Golen, J. A.; Rheingold, A. L.; Nataro, C. Organometallics 2006, 25, 4292.
40. (d) Hagopian, L. E.; Campbell, A. N.; Golen, J. A.; Rheingold, A. L.; Nataro, C. J. Organomet. Chem. 2006, 691, 4890.
41. (e) Khan, S. L.; Breheney, M. K.; Martinak, S. L.; Fosbenner, S. M.; Seibert, A. R.; Kassel, W. S.; Dougherty, W. G.; Nataro, C. Organometallics 2009, 28, 2119.
42. (a) Ghent, B. L.; Sites, L. A.; Rheingold, A. L.; Nataro, C. Organometallics 2005, 24, 4788.
43. (b) Ghent, B. L.; Martinak, S. L.; Sites, L. A.; Golen, J. A.; Rheingold, A. L.; Nataro, C. J. Organomet. Chem. 2007, 692, 2365.
44. (c) Maddox, A. F.; Rheingold, A. L.; Golen, J. A.; Kassel, W. S.; Nataro, C. Inorg. Chim. Acta 2008, 361, 3283.
45. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518.
46. Gusev, O. V.; Peterleitner, M. G.; Kal'sin, A. M.; Vologdin, N. V. Russ. J. Electrochem. 2003, 39, 1293.
47. (a) Lu, S.; Strelets, V. V.; Ryan, M. F.; Pietro, W. J.; Lever, A. B. P. Inorg. Chem. 1996, 35, 1013; From this reference, Fc=0.66VvsNHE.
48. (b) Lever, A. B. P. In Comprehensive Coordination Chemistry, 2nd ed.; McCleverty, J. A., Meyer, T. J., Eds.; Elsevier Science: New York, 2004, Vol. 2, p 251.
49. (a) Mather, G. G.; Pidcock, A.; Rapsey, G. J. N. J. Chem. Soc, Dalton Trans. 1973, 2095.
50. (b) Blau, R. J.; Espenson, J. H. Inorg. Chem. 1986, 25, 878.
51. (c) Heuer, L.; Jones, P. G.; Schomburg, D.; Schmutzler, R. Phosphorus, Sulfur Silicon Relat. Elem. 1990, 49/50, 421.
52. (a) Arnold, D. P.; Bennett, M. A. Inorg. Chem. 1984, 23, 2117.
53. (b) Manojlović-Muir, L.; Muir, K. W.; Solomun, T. J. Organomet. Chem. 1977, 142, 265.
54. (c) Hitchcock, P. B.; Jacobson, B.; Pidcock, A. J. Chem. Soc, Dalton Trans. 1977, 2038.
55. (d) Béni, Z.; Ros, R.; Tassan, A.; Scopelliti, R.; Roulet, R. Inorg. Chim. Acta 2005, 358, 497.
56. (a) Poater, A.; Cosenza, B.; Correa, A.; Giudice, S.; Ragone, F.; Scarano, V.; Cavallo, L. Eur. J. Inorg. Chem. 2009, 1759.
57. (b) http://www.molnac.unisa.it/OMtools/sambvca.php.
58. Clavier, H.; Nolan, S. P. Chem. Commun. 2010, 46, 841.
59. Muller, A. Acta Crystallogr., Sect. E: Struct. Rep. Online 2007, 63, m210.
60. Li, S.; Wei, B.; Low, P. M. N.; Lee, H. K.; Hor, T. S. A.; Xue, F.; Mak, T. C. W. J. Chem. Soc., Dalton Trans. 1997, 1289.
61. Fihri, A.; Hierso, J.-C.; Vion, A.; Nguyen, D. H.; Urrutigoity, M.; Kalck, P.; Amardeil, R.; Meunier, P. Adv. Synth. Catal. 2005, 347, 1198.
62. Fihri, A.; Boudon, J.; Hierso, J.-C.; Amardeil, R.; Meunier, P.; Richard, P. Acta Crystallogr., Sect. E: Struct. Rep. Online 2005, 61, m2267.
63. Velazco, E. J.; Caffyn, A. J. M. Organometallics 2008, 27, 2402.
64. Seibert, A. R.; Dougherty, W. G.; Kassel, W. S.; Nataro, C. Inorg. Chim. Acta, in press; http://dx.doi.org/10.1016/j.ica.2010.06.061
65. Babai, A.; Deacon, G. B.; Erven, A. P.; Meyer, G. Z. Anorg. Allg. Chem. 2006, 632, 639.
66. Bovio, B.; Bonati, F.; Banditelli, G. Gazz. Chim. Ital 1985, 115, 613.
67. Kaim, W.; Dogan, A.; Klein, A.; Zalis, S. Z. Anorg. Allg. Chem. 2005, 631, 1355.
68. Deacon, G. B.; Elliott, P. W.; Erven, A. P.; Meyer, G. Z. Anorg. Allg. Chem. 2005, 631, 843.
69. Klein, H.-P.; Thewalt, U.; Zettlmeissl, H.; Brune, H. A. Z. Naturforsch., B: Chem. Sci. 1981, 36, 1125.
70. Mague, J. T.; Fink, M. J.; Recatto, C. A. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1993, 49, 1176.
71. Otero, A.; Carrillo-Hermosilla, F.; Terreros, P.; Exposito, T.; Rojas, S.; Fernandez-Baeza, J.; Antinolo, A.; Lopez-Solera, I. Eur. J. Inorg. Chem. 2003, 3233.
72. Gunay, A.; Brennessel, W. W.; Jones, W. D. Acta Crystallogr., Sect. E: Struct. Rep. Online 2008, 64, m454.
73. Oberhauser, W.; Bachmann, C.; Stampfl, T.; Haid, R.; Langes, C.; Rieder, A.; Bruggeller, P. Inorg. Chim. Acta 1998, 274, 143.
74. Yamamoto, Y.; Fukui, Y.; Matsubara, K.; Takeshima, H.; Miyauchi, F.; Tanase, T.; Yamamoto, G. J. Chem. Soc., Dalton Trans. 2001, 1773.
75. Bracher, G.; Grove, D. M.; Venanzi, L. M.; Bachechi, F.; Mura, P.; Zambonelli, L. Helv. Chim. Acta 1980, 63, 2519.
76. Mikami, K.; Kakuno, H.; Aikawa, K. Angew. Chem., Int. Ed. 2005, 44, 7257.
77. Doherty, S.; Knight, J. G.; Smyth, C. H.; Harrington, R. W.; Clegg, W. J. Org. Chem. 2006, 71, 9751.
78. Wicht, D. K.; Zhuravel, M. A.; Gregush, R. V.; Glueck, D. S.; Guzei, I. A.; Liable-Sands, L. M.; Rheingold, A. L. Organometallics 1998, 17, 1412.
79. Fang, Z.-G.; Hor, T. S. A.; Wen, Y.-S.; Liu, L.-K.; Mak, T. C. W. Polyhedron 1995, 14, 2403.
80. Pilloni, G.; Longato, B.; Bandoli, G.; Corain, B. J. Chem. Soc, Dalton Trans. 1997, 819.
81. Necas, M.; Beran, M.; Woollins, J. D.; Novosad, J. Polyhedron 2001, 20, 741.
82. Kahn, S. L.; Breheney, M. K.; Martinak, S. L.; Fosbenner, S. M.; Seibert, A. R.; Kassel, W. S.; Dougherty, W. G; Nataro, C. Organometallics 2009, 28, 2119.
83. Average P-S and P-Se bond lengths based on analysis of the Cambridge Crystallographic Database on September 8, 2010.
84. Fernändez-Galän, R.; Manzano, B. R; Otero, A.; Lanfranchi, M.; Pellinghelli, M. A. Inorg. Chem. 1994, 33, 2309.
85. Stec, W. J.; Okruszek, A.; Michalski, J. J. Org. Chem. 1976, 41, 233.