Two [1,2,4-(Me3C)3C5H2] 2CeH molecules are involved in hydrogenation of pyridine to piperidine as shown by experiments and computations

Inorganic Chemistry

Volumn 53, Issue 13, 2014, Pages 6361-6373

  Perrin, Lionel ^a,b,e   Werkema, Evan L ^c   Eisenstein, Odile ^d   Andersen, Richard A ^c  

^a UNIVERSITÉ DE TOULOUSE   (France)

^b CNRS   (France)

^c UNIVERSITY OF CALIFORNIA   (United States)

^d UNIVERSITÉ DE MONTPELLIER   (France)

^e UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84903973499     PISSN: 00201669     EISSN: 1520510X     Source Type: Journal    
DOI: 10.1021/ic500133y     Document Type: Article

References (61)

1. Sánchez-Delgado, R. A. Organometallic modeling of the hydrodesulfurization and hydrodenitrogenation reactions; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2002.
2. Toshiaki, K.; Atsushi, I.; Weihua, Q. Hydrodesulfurization and hydrodenitrogenation: chemistry and engineering; Wiley-VCH: Tokyo, 1999.
3. Crabtree, R. H. Energy Environ. Sci. 2008, 1, 134-138
4. Ali, S. A. In Hydroprocessing of Heavy Oils and Residua; Speight, J. G.; Ancheyta, J., Eds.; CRC Press: Boca Raton, FL, 2007; Chapter 4.
5. The black values are from ref 4a; the red values were extracted from: Cocchetto, J. F.; Satterfield, C. N. Ind. Eng. Chem., Process. Des. Dev. 1976, 15, 272-277. The blue values are computed at the MO6-2X DFT level (see the SI)
6. Rahi, R.; Fang, M.; Ahmed, A.; Sánchez-Delgado, R. A. Dalton Trans. 2012, 41, 14490-14497
7. Girgis, M. J.; Gates, B. C. Ind. Eng. Chem. Res. 1991, 30, 2021-2058
8. Busca, G. Chem. Rev. 2007, 107, 5366-5410
9. Glorius, F. Org. Biomol. Chem. 2005, 3, 4171-4175
10. Wang, D.-S.; Chen, Q.-A.; Lu, S.-M.; Zhou, Y.-G. Chem. Rev. 2012, 112, 2557-2590
11. Yu, Z.; Jin, W.; Jiang, Q. Angew. Chem., Int. Ed. 2012, 51, 6060-6072
12. Sonnemans, J.; Van den Berg, G. H.; Mars, P. J. Catal. 1973, 31, 220-230
13. Kliewer, C. J.; Somorjai, G. A. Catal. Lett. 2010, 137, 118-122
14. Kliewer, C. J.; Bieri, M.; Somorjai, G. A. J. Phys. Chem. C 2008, 112, 11373-11378
15. Li, Y.; Guo, W.; Zhu, H.; Zhao, L.; Li, M.; Li, S.; Fu, D.; Lu, X.; Shan, H. Langmuir 2012, 28, 3129-3137
16. Weller, K. J.; Fox, P. A.; Gray, S. D.; Wigley, D. E. Polyhedron 1997, 16, 3139-3163
17. Bianchini, C.; Meli, A.; Vizza, F. Eur. J. Inorg. Chem. 2001, 43-68
18. Dobereiner, G.; Nova, A.; Schley, N.; Hazari, N.; Miller, S.; Eisenstein, O.; Crabtree, R. H. J. Am. Chem. Soc. 2011, 133, 7547-7562
19. Sánchez-Delgado, R. A.; Ronden, D.; Andriollo, A.; Herrera, V.; Martin, G.; Chaudret, B. Organometallics 1993, 12, 4291-4296
20. Rosales, M.; Vallejo, R.; Soto, J. J.; Bastidas, L. J.; Molina, K.; Baricelli, P. J. Catal. Lett. 2010, 134, 56-62
21. Rosales, M.; Alvarado, Y.; Boves, M.; Rubio, R.; Soscun, H.; Sánchez-Delgado, R. A. Transition Met. Chem. 1995, 20, 246-251
22. Bianchini, C.; Barbaro, P.; Macchi, M.; Meli, A.; Vizza, F. Helv. Chim. Acta 2001, 84, 2895-2932
23. Magee, M. P.; Norton, J. R. J. Am. Chem. Soc. 2001, 123, 1778-1779
24. Bullock, R. M. Chem. - Eur. J. 2004, 10, 2366-2374
25. Guan, H.; Iimura, M.; Magee, M. P.; Norton, J. R.; Zhu, G. J. Am. Chem. Soc. 2005, 127, 7805-7814
26. Zhou, H.; Li, Z.; Wang, Z.; Wang, T.; Xu, L.; He, Y.; Fan, Q.-H.; Pan, J.; Gu, L.; Chan, A. S. C. Angew. Chem., Int. Ed. 2008, 47, 8464-8467
27. Eisenstein, O.; Crabtree, R. H. New J. Chem. 2013, 37, 21-27
28. Jardine, I.; McQuillin, F. J. J. Chem. Soc., Chem. Commun. 1970, 626
29. Baralt, E.; Smith, S. J.; Hurwitz, J.; Horvath, I. T.; Fish, R. H. J. Am. Chem. Soc. 1992, 114, 5187-5196
30. Borowski, A. F.; Sabo-Etienne, S.; Donnadieu, B.; Chaudret, B. Organometallics 2003, 22, 4803-4809
31. Berno, P.; Gambarotta, S. Organometallics 1994, 13, 2569-2571
32. Watson, P. L. J. Chem. Soc., Chem. Commun. 1983, 276-277
33. Deelman, B.-J.; Stevels, W. M.; Teuben, J. H.; Lakin, M. T.; Spek, A. L. Organometallics 1994, 13, 3881-3891
34. Thompson, M. E.; Baxter, S. M.; Bulls, A. R.; Burger, B. J.; Nolan, M. C.; Santarsiero, B. D.; Schaefer, W. P.; Bercaw, J. E. J. Am. Chem. Soc. 1987, 109, 203-219
35. Evans, W. J.; Hughes, L. A.; Hanusa, T. P. J. Am. Chem. Soc. 1984, 106, 4270-4271
36. Diaconescu, P. L. Curr. Org. Chem. 2008, 12, 1388-1405
37. Werkema, E. L.; Andersen, R. A.; Yahia, A.; Maron, L.; Eisenstein, O. Organometallics 2009, 28, 3173-3185
38. Booth, H.; Everett, J. R. J. Chem. Soc., Chem. Commun. 1979, 34-35
39. Heeres, H. J.; Meetsma, A.; Teuben, J. H.; Rogers, R. D. Organometallics 1989, 8, 2637-2646
40. Hitchcock, P. B.; Lappert, M. F.; Protchenko, A. V. Chem. Commun. 2006, 3546-3548
41. Fjeldberg, T.; Andersen, R. A. J. Mol. Struct. 1985, 129, 93-105
42. Werkema, E. L.; Andersen, R. A.; Maron, L.; Eisenstein, O. Dalton Trans. 2010, 39, 6648-6660
43. Gundersen, G.; Rankin, D. W. H. Acta Chem. Scand., Ser. A 1983, 37, 865-874
44. Brookhart, M.; Green, M. L. H. J. Organomet. Chem. 1983, 250, 395-408
45. Brookhart, M.; Green, M. L. H.; Wong, L. L. Prog. Inorg. Chem. 1988, 36, 1-124
46. Brookhart, M.; Green, M. L. H.; Parkin, G. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 6908-6914
47. Clot, E.; Eisenstein, O. In Principles and Applications of Density Functional Theory in Inorganic Chemistry II; Kaltsoyannis, N.; McGrady, J. E., Eds.; Structure and Bonding Series; Springer-Verlag: Heidelberg, Germany, 2004; Vol. 113, pp 1-36.
48. Balcells, D.; Clot, E.; Eisenstein, O. Chem. Rev. 2010, 110, 749-823
49. Scherer, W.; Herz, V.; Hauf, C. Structure and Bonding (Berlin); Springer-Verlag: Heidelberg, Germany, 2012; Vol. 146, pp 159-208.
50. Lein, M. Coord. Chem. Rev. 2009, 253, 625-634
51. Pauling, L. The Nature of the Chemical Bond, 3rd ed.; Cornell University Press: Ithaca, NY, 1960.
52. Maron, L.; Werkema, E. L.; Perrin, L.; Eisenstein, O.; Andersen, R. A. J. Am. Chem. Soc. 2005, 127, 279-292
53. Werkema, E. L.; Maron, L.; Eisenstein, O.; Andersen, R. A. J. Am. Chem. Soc. 2007, 129, 2529-2541 (correction on p 6662)
54. Werkema, E. L.; Yahia, A.; Maron, L.; Eisenstein, O.; Andersen, R. A. Organometallics 2010, 29, 5103-5110
55. Werkema, E. L.; Castro, L.; Maron, L.; Eisenstein, O.; Andersen, R. A. Organometallics 2012, 31, 870-881
56. Werkema, E. L.; Castro, L.; Maron, L.; Eisenstein, O.; Andersen, R. A. New J. Chem. 2013, 37, 132-142
57. Schafman, B. S.; Wenthold, P. G. J. Org. Chem. 2007, 72, 1645-1651
58. Wren, S. W.; Vogelhuber, K. M.; Garver, J. M.; Kato, S.; Sheps, L.; Bierbaum, M.; Lineberger, W. C. J. Am. Chem. Soc. 2012, 134, 6584-6595
59. Moellmann, J.; Grimme, S. Organometallics 2013, 32, 3784-3787
60. Werkema, E. L.; Yahia, A.; Maron, L.; Eisenstein, O.; Andersen, R. A. New J. Chem. 2010, 34, 2189-2196
61. Werkema, E. L.; Messines, E.; Perrin, L.; Maron, L.; Eisenstein, O.; Andersen, R. A. J. Am. Chem. Soc. 2005, 127, 7781-7795