Proton-controlled regioselective synthesis of [Cp∗(dppe)Fe-C≡C-1-(η6-C10H7)Ru(η5-Cp](PF6) and electron-driven haptotropic rearrangement of the (η5-Cp)Ru+ arenophile

Organometallics

Volumn 33, Issue 18, 2014, Pages 4792-4802

  Makhoul, Rim ^a   Sahnoune, Hiba ^a   Davin, Thomas ^a   Kahlal, Samia ^a   Dorcet, Vincent ^a   Roisnel, Thierry ^a   Halet, Jean François ^a   Hamon, Jean René ^a   Lapinte, Claude ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENERGY; CHEMICAL ACTIVATION; CHLORINE COMPOUNDS; COORDINATION REACTIONS; CYCLIC VOLTAMMETRY; DENSITY FUNCTIONAL THEORY; IRON; ISOMERS; MOLECULES; NAPHTHALENE; ORGANIC SOLVENTS; REGIOSELECTIVITY; RUBIDIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

COORDINATING SOLVENTS; HAPTOTROPIC REARRANGEMENTS; HETEROBINUCLEAR COMPLEXES; ONE-ELECTRON OXIDATION; REACTION PATHWAYS; REGIOSELECTIVE SYNTHESIS; THEORETICAL CALCULATIONS; X RAY CRYSTAL STRUCTURES;

IRON COMPOUNDS;

EID: 84910012980     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om500047k     Document Type: Article

References (65)

1. Astruc, D. Electron Transfer and Radical Processes in Transition-Metal Chemistry; VCH: New York, 1995.
2. (a) Jortner, J.; Ratner, M. A. Molecular Electronics; Blackwell Science: Oxford, U.K., 1997.
3. (b) Aviram, A.; Ratner, M. A. Ann. N.Y. Acad. Sci. 1998, 852.
4. (c) Ratner, M. Nature 2000, 404, 137.
5. (d) Tour, J. M. Acc. Chem. Res. 2000, 33, 791-803.
6. (e) Hipps, K. W. Science 2001, 294, 536-537.
7. (f) Cahen, D.; Hodes, G. Adv. Mater. 2002, 14, 789.
8. (g) Caroll, R. L.; Gorman, C. B. Angew. Chem., Int. Ed. 2002, 41, 4379-4400.
9. (h) Robertson, N.; McGowan, G. A. Chem. Soc. Rev. 2003, 32, 96-103.
10. (i) Flood, A. H.; Stoddart, J. F.; Steuerman, D. W.; Heath, J. R. Science 2004, 306, 2055-2056.
11. (j) Szacilowski, K. Chem. Rev. 2008, 108, 3481.
12. Paul, F.; Lapinte, C. Coord. Chem. Rev. 1998, 178-180, 427-505.
13. Irie, M. Chem. Rev. 2000, 100, 1685-1716.
14. (a) Muriuchi, A.; Uchida, K.; Inagaki, A.; Akita, M. Organometallics 2005, 24, 6382-6392.
15. (b) Takano, K.; Inagaki, A.; Akita, M. Chem. Lett. 2006, 35, 434-435.
16. (c) Uchida, K.; Inagaki, A.; Akita, M. Organometallics 2007, 26, 5030-5041.
17. (d) Tanaka, Y.; Ishisaka, T.; Inagaki, A.; Koike, T.; Lapinte, C.; Akita, M. Chem. Eur. J. 2010, 16, 4762-4776.
18. (e) Wong, K. M.-C.; Lam, S. C.-F.; Ko, C.-C.; Zhu, N.; Yam, V. W.-W.; Roue, S.; Lapinte, C.; Fathallah, S.; Costuas, K.; Kahlal, S.; Halet, J.-F. Inorg. Chem. 2003, 42, 7086-7097.
19. (f) Samoc, M.; Gauthier, N.; Cifuentes, M. P.; Paul, F.; Lapinte, C.; Humphrey, M. G. Angew. Chem., Int. Ed. 2006, 45, 7376-7379.
20. (g) Weyland, T.; Ledoux, I.; Brasselet, S.; Zyss, J.; Lapinte, C. Organometallics 2000, 19, 5235-5237.
21. (a) Jahr, H. C.; Nieger, M.; Dotz, K. H. Chem. Commun. 2003, 2866-2867.
22. (b) Dotz, K. H.; Jahr, H. C. Chem. Rec. 2004, 4, 61-71.
23. (c) Jahr, H. C.; Nieger, M.; Dotz, K. H. Chem. Eur. J. 2005, 11, 5333-5342.
24. Pan, J.; Kampf, J. W.; Ashe, A. J. Organometallics 2006, 25, 3463-3467.
25. Oprunenko, Y. F. Russ. Chem. Rev. 2000, 69, 683-704.
26. Pan, J.; Kampf, J. W.; Ashe, A. J. Organometallics 2006, 25, 197-202.
27. Perekalin, D. S.; Karslyan, E. E.; Petrovskii, P. V.; Borissova, A. O.; Lyssenko, K. A.; Kudinov, A. R. Eur. J. Inorg. Chem. 2012, 1485-1492.
28. Shaw-Taberlet, J. A.; Sinbandit, S.; Roisnel, T.; Hamon, J.-R.; Lapinte, C. Organometallics 2006, 25, 5311-5325.
29. Denis, R.; Toupet, L.; Paul, F.; Lapinte, C. Organometallics 2000, 19, 4240-4251.
30. Hubig, S. M.; Lindeman, S. V.; Kochi, J. K. Coord. Chem. Rev. 2000, 200-202, 831-873.
31. (a) Koefod, R. S.; Mann, K. R. J. Am. Chem. Soc. 1990, 112, 7287-7293.
32. (b) Nolan, S. P.; Martin, K. L.; Stevens, E. D.; Fagan, P. J. Organometallics 1992, 11, 3947-3953.
33. (c) Fagan, P. J.; Ward, M. D.; Calabrese, J. C.; Caspar, J. V.; Krusic, P. J. J. Am. Chem. Soc. 1988, 110, 2981-2963.
34. Paul, F.; Toupet, L.; Thepot, J.-Y.; Costuas, K.; Halet, J.-F.; Lapinte, C. Organometallics 2005, 24, 5464-5478.
35. Paul, F.; Mevellec, J.-Y.; Lapinte, C. Dalton Trans. 2002, 1783-1790.
36. Justaud, F.; Gendron, F.; Ogyu, Y.; Kumamoto, Y.; Miyazaki, A.; Ouahab, L.; Costuas, K.; Halet, J.-F.; Lapinte, C. Chem. Eur. J. 2013, 19, 5742-5757.
37. Lapinte, C.; Catheline, D.; Astruc, D. Organometallics 1984, 3, 817-819.
38. (a) Hamon, P.; Toupet, L.; Hamon, J.-R.; Lapinte, C. Organometallics 1996, 15, 10-12.
39. (b) Roger, C.; Hamon, P.; Toupet, L.; Rabaa, H.; Saillard, J.-Y.; Hamon, J.-R.; Lapinte, C. Organometallics 1991, 10, 1045-1054.
40. Elschenbroich, C. Organometallics; Wiley-VCH: Weinheim, Germany, 2006.
41. (a) Morokuma, K. J. Chem. Phys. 1971, 55, 1224-1236.
42. (b) Ziegler, T.; Rauk, A. Theor. Chem. Acta 1977, 46, 1-10.
43. (c) Ziegler, T.; Rauk, A. Inorg. Chem. 1979, 18, 1558-1565.
44. (d) Ziegler, T.; Rauk, A. Inorg. Chem. 1979, 18, 1755-1759.
45. (e) Bickelhaupt, F. M.; Baerends, E. J. Rev. Comput. Chem. 2000, 15, 1-86.
46. (a) Gridnev, I. D. Coord. Chem. Rev. 2008, 252, 1798-1818.
47. (b) Freedman, D. A.; Gill, T. P.; Blough, A. M.; Koefod, R. S.; Mann, K. R. Inorg. Chem. 1997, 36, 95-102.
48. (c) Kundig, E. P.; Jeger, P.; Bernardinelli, G. Inorg. Chim. Acta 2004, 357, 1909-1919.
49. (d) Deramchi, K.; Maouche, B.; Fadel, L.; Kahlal, S.; Saillard, J.-Y. Inorg. Chim. Acta 2012, 391, 98-104.
50. (e) Fetisov, E. O.; Gloriozov, I. P.; Oprunenko, Y. F.; Saillard, J.-Y.; Kahlal, S. Organometallics 2013, 32, 3512-3520.
51. Albright, T. A.; Hofmann, P.; Hoffmann, R.; Lillya, C. P.; Dobosh, P. A. J. Am. Chem. Soc. 1983, 105, 3396-3411.
52. +. See: Perekalin, D. S.; Karslyan, E. E.; Trifonova, E. A.; Konovalov, A. I.; Loskutova, N. L.; Yulia V. Nelyubina, Y. V.; Kudinov, A. R. Eur. J. Inorg. Chem. 2013, 481-493.
53. (a) Trost, B. M.; Older, C. M. Organometallics 2002, 21, 2544-2546.
54. (b) Grepioni, F.; Cojazzi, G.; Braga, D.; Marseglia, E. A.; Scaccianoce, L.; Johnson, B. F. G. J. Chem. Soc., Dalton Trans. 1999, 553-558.
55. Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877-910.
56. Altomare, A.; Burla, M. C.; Camali, M.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 31, 115-119.
57. Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112-118.
58. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837-838.
59. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision A.02; Gaussian, Inc., Wallingford, CT, 2009.
60. Zhao, Y.; Truhlar, D. G. J. Chem. Phys. 2006, 125, 194101.
61. Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 299-310.
62. Fukui, K. J. Acc. Chem. Res. 1981, 14, 363-368.
63. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999-3093.
64. (a) Molekel 4.3; Flukiger, P., Luthi, H. P., Portmann, S., Weber, J., Eds.; Swiss Center for Scientific Computing, Manno, Switzerland, 2000; http://www.cscs.ch/molkel.
65. (b) Portmann, S.; Luthi, H. P. Chimia 2000, 54, 766-770.