Ruthenium bidentate phosphine complexes for the coordination and catalytic dehydrogenation of amine- and phosphine-boranes

Chemistry - A European Journal

Volumn 17, Issue 31, 2011, Pages 8704-8713

  Ledger, Araminta E W ^a   Ellul, Charles E ^a   Mahon, Mary F ^a   Williams, Jonathan M J ^a   Whittlesey, Michael K ^a  

^a University of Bath Claverton Down   (United Kingdom)

Author keywords

agostic interactions; amine boranes; dehydrogenation; N heterocyclic carbenes; phosphine ligands; phosphine boranes; ruthenium

Indexed keywords

AGOSTIC INTERACTIONS; AMINE-BORANES; N-HETEROCYCLIC CARBENES; PHOSPHINE LIGANDS; PHOSPHINE-BORANES;

BORON COMPOUNDS; CARBON INORGANIC COMPOUNDS; COMPLEXATION; COORDINATION REACTIONS; DEHYDROGENATION; HYDRIDES; IRON COMPOUNDS; ORGANIC COMPOUNDS; PHOSPHORUS COMPOUNDS; RUTHENIUM;

RUTHENIUM COMPOUNDS;

EID: 79960479843     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201100101     Document Type: Article

References (85)

1. T. J. Clark, K. Lee, I. Manners, Chem. Eur. J. 2006, 12, 8634-8648
2. C. W. Hamilton, R. T. Baker, A. Staubitz, I. Manners, Chem. Soc. Rev. 2009, 38, 279-293
3. N. C. Smythe, J. C. Gordon, Eur. J. Inorg. Chem. 2010, 509-521
4. A. Staubitz, A. P. M. Robertson, M. E. Sloan, I. Manners, Chem. Rev. 2010, 110, 4023-4078
5. A. Staubitz, A. P. M. Robertson, I. Manners, Chem. Rev. 2010, 110, 4079-4124
6. A. Staubitz, M. E. Sloan, A. P. M. Robertson, A. Friedrich, S. Schneider, P. J. Gates, J. S. auf der Günne, I. Manners, J. Am. Chem. Soc. 2010, 132, 13332-13345.
7. H. Dorn, J. M. Rodezno, B. Brunnhöfer, E. Rivard, J. A. Massey, I. Manners, Macromolecules 2003, 36, 291-297.
8. H. Dorn, R. A. Singh, J. A. Massey, A. J. Lough, I. Manners, Angew. Chem. 1999, 111, 3540-3543
9. Angew. Chem. Int. Ed. 1999, 38, 3321-3323
10. C. A. Jaska, K. Temple, A. J. Lough, I. Manners, Chem. Commun. 2001, 962-963
11. C. A. Jaska, K. Temple, A. J. Lough, I. Manners, J. Am. Chem. Soc. 2003, 125, 9424-9434
12. C. A. Jaska, I. Manners, J. Am. Chem. Soc. 2004, 126, 2698-2699
13. C. A. Jaska, I. Manners, J. Am. Chem. Soc. 2004, 126, 9776-9785
14. M. C. Denney, V. Pons, T. J. Hebden, D. M. Heinekey, K. I. Goldberg, J. Am. Chem. Soc. 2006, 128, 12048-12049
15. R. J. Keaton, J. M. Blacquiere, R. T. Baker, J. Am. Chem. Soc. 2007, 129, 1844-1845
16. Y. Jiang, H. Berke, Chem. Commun. 2007, 3571-3573
17. B. L. Dietrich, K. I. Goldberg, D. M. Heinekey, T. Autrey, J. C. Linehan, Inorg. Chem. 2008, 47, 8583-8585
18. N. Blaquiere, S. Diallo-Garcia, S. I. Gorelsky, D. A. Black, K. Fagnou, J. Am. Chem. Soc. 2008, 130, 14034-14035
19. Y. Jiang, O. Blacque, T. Fox, C. M. Frech, H. Berke, Organometallics 2009, 28, 5493-5504
20. Y. Kawano, M. Uruichi, M. Shimoi, S. Taki, T. Kawaguchi, T. Kakizawa, H. Ogino, J. Am. Chem. Soc. 2009, 131, 14946-14957
21. A. Friedrich, M. Drees, S. Schneider, Chem. Eur. J. 2009, 15, 10339-10342
22. M. Käß, A. Friedrich, M. Drees, S. Schneider, Angew. Chem. 2009, 121, 922-924
23. Angew. Chem. Int. Ed. 2009, 48, 905-907
24. P. M. Zimmerman, A. Paul, Z. Zhang, C. B. Musgrave, Angew. Chem. 2009, 121, 2235-2239
25. Angew. Chem. Int. Ed. 2009, 48, 2201-2205
26. M. E. Sloan, A. Staubitz, T. J. Clark, C. A. Russell, G. C. Lloyd-Jones, I. Manners, J. Am. Chem. Soc. 2010, 132, 3831-3841
27. S. K. Kim, W. S. Han, T. J. Kim, T. Y. Kim, S. W. Nam, M. Mitoraj, L. Piekos, A. Michalak, S. J. Hwang, S. O. Kang, J. Am. Chem. Soc. 2010, 132, 9954-9955
28. C. Boulho, J. P. Djukic, Dalton Trans. 2010, 39, 8893-8905
29. M. Zahmakiran, M. Tristany, K. Philippot, K. Fajerwerg, S. Ozkar, B. Chaudret, Chem. Commun. 2010, 46, 2938-2940.
30. For recent reviews, see: G. Alcaraz, M. Grellier, S. Sabo-Etienne, Acc. Chem. Res. 2009, 42, 1640-1649
31. G. Alcaraz, S. Sabo-Etienne, Angew. Chem. 2010, 122, 7326-7335
32. Angew. Chem. Int. Ed. 2010, 49, 7170-7179.
33. T. M. Douglas, A. B. Chaplin, A. S. Weller, J. Am. Chem. Soc. 2008, 130, 14432-14433
34. R. Dallanegra, A. B. Chaplin, A. S. Weller, Angew. Chem. 2009, 121, 7007-7010
35. Angew. Chem. Int. Ed. 2009, 48, 6875-6878
36. T. M. Douglas, A. B. Chaplin, A. S. Weller, X. Z. Yang, M. B. Hall, J. Am. Chem. Soc. 2009, 131, 15440-15456
37. Y. Gloaguen, G. Alcaraz, A-F. Pécharman, E. Clot, L. Vendier, S. Sabo-Etienne, Angew. Chem. 2009, 121, 3008-3012
38. Angew. Chem. Int. Ed. 2009, 48, 2964-2968
39. G. Alcaraz, L. Vendier, E. Clot, S. Sabo-Etienne, Angew. Chem. 2010, 122, 930-932
40. Angew. Chem. Int. Ed. 2010, 49, 918-920
41. A. B. Chaplin, A. S. Weller, Angew. Chem. 2010, 122, 591-594
42. Angew. Chem. Int. Ed. 2010, 49, 581-584
43. R. Dallanegra, A. B. Chaplin, J. Tsim, A. S. Weller, Chem. Commun. 2010, 46, 3092-3094
44. A. B. Chaplin, A. S. Weller, Inorg. Chem. 2010, 49, 1111-1121
45. C. Y. Tang, A. L. Thompson, S. Aldridge, J. Am. Chem. Soc. 2010, 132, 10578-10591
46. C. Y. Tang, A. L. Thompson, S. Aldridge, Angew. Chem. 2010, 122, 933-937
47. Angew. Chem. Int. Ed. 2010, 49, 921-925.
48. A. E. W. Ledger, A. Moreno, C. E. Ellul, M. F. Mahon, P. S. Pregosin, M. K. Whittlesey, J. M. J. Williams, Inorg. Chem. 2010, 49, 7244-7256.
49. M. Shimoi, S. Nagai, M. Ichikawa, Y. Kawano, K. Katoh, M. Uruichi, H. Ogino, J. Am. Chem. Soc. 1999, 121, 11704-11712.
50. T. Yasue, Y. Kawano, M. Shimoi, Angew. Chem. 2003, 115, 1769-1772
51. Angew. Chem. Int. Ed. 2003, 42, 1727-1730
52. Y. Kawano, M. Hashiva, M. Shimoi, Organometallics 2006, 25, 4420-4426
53. C. M. Nagaraja, P. Parameswaran, E. D. Jemmis, B. R. Jagirdar, J. Am. Chem. Soc. 2007, 129, 5587-5596
54. Y. Kawano, K. Yamaguchi, S. Y. Miyake, T. Kakizawa, M. Shimoi, Chem. Eur. J. 2007, 13, 6920-6931.
55. 1-H-B amidoborane ligand resulting from a proton transfer from ammonia borane to a ruthenium-bound amido ligand. See reference [3i].
56. 2tBu ligand.
57. 2] as this is known to be insoluble. See reference [3i] and references therein.
58. M. Ingleson, N. J. Patmore, G. D. Ruggiero, C. G. Frost, M. F. Mahon, M. C. Willis, A. S. Weller, Organometallics 2001, 20, 4434-4436
59. O. Volkov, R. Macías, N. P. Rath, L. Barton, Inorg. Chem. 2002, 41, 5837-5843
60. N. Merle, G. Kociok-Köhn, C. G. Frost, G. D. Ruggiero, A. S. Weller, M. C. Willis, Dalton Trans. 2004, 3883-3892.
61. M. A. Frisch, H. G. Heal, H. Mackle, I. O. Madden, J. Chem. Soc. 1965, 899-907
62. A. C. Gaumont, B. Carboni, Sci. Synth. 2004, 6, 485-512.
63. K. Lee, T. J. Clark, A. J. Lough, I. Manners, Dalton Trans. 2008, 2732-2740.
64. 3 interaction. See reference [6].
65. 1H NMR spectroscopy; after 72 h at room temperature, 4 was still present along with a number of new Ru-H products.
66. 4=1,3,4,5-tetramethylimidazol-2-ylidene; ICy=1,3- dicyclohexylimidazol-2-ylidene; IAd=1,3-diadamantylimidazol-2-ylidene.
67. W. Baratta, E. Herdtweck, P. Rigo, Angew. Chem. 1999, 111, 1733-1735
68. Angew. Chem. Int. Ed. 1999, 38, 1629-1631
69. Angew. Chem. 1999, 111, 1629-1631
70. D. Huang, W. E. Streib, J. C. Bollinger, K. G. Caulton, R. F. Winter, T. Scheiring, J. Am. Chem. Soc. 1999, 121, 8087-8097
71. K. Abdur-Rashid, T. Fedorkiw, A. J. Lough, R. H. Morris, Organometallics 2004, 23, 86-94.
72. S. Burling, G. Kociok-Köhn, M. F. Mahon, M. K. Whittlesey, J. M. J. Williams, Organometallics 2005, 24, 5868-5878
73. S. Burling, E. Mas-Marzá, J. E. V. Valpuesta, M. F. Mahon, M. K. Whittlesey, Organometallics 2009, 28, 6676-6686.
74. M. B. Dinger, P. Nieczypor, J. C. Mol, Organometallics 2003, 22, 5291-5296.
75. L. Pasumansky, D. Haddenham, J. W. Clary, G. B. Fisher, C. T. Goralski, B. Singaram, J. Org. Chem. 2008, 73, 1898-1905.
76. 2 precluded accurate volumetric measurements.
77. Both of these experiments were run with a faster stirrer speed compared to those shown in Figure 6. This accounts for the slightly different appearance of the two traces employing 2.5 mol % 12.
78. The use of a third-generation Grubbs catalyst in the dehydrogenation of methylamine-borane has been reported briefly. See reference [1f].
79. X. Yang, M. B. Hall, J. Am. Chem. Soc. 2008, 130, 1798-1799
80. X. Yang, M. B. Hall, J. Organomet. Chem. 2009, 694, 2831-2838.
81. R. A. Schunn, E. R. Wonchoba, G. Wilkinson, Inorg. Synth. 1972, 13, 131-134.
82. S. P. Nolan, personal communication.
83. + by comparison to previous work:, S. Burling, L. J. L. Häller, E. Mas-Marzá, A. Moreno, S. A. Macgregor, M. F. Mahon, P. S. Pregosin, M. K. Whittlesey, Chem. Eur. J. 2009, 15, 10912-10923.
84. G. M. Sheldrick, Acta. Cryst. A 1990, 46, 467-473
85. Sheldrick, G. M. SHELXL-97, a computer program for crystal structure refinement, University of Göttingen, 1997.