Heterogeneous dehydrocoupling of amine-borane adducts by skeletal nickel catalysts

Inorganic Chemistry

Volumn 50, Issue 24, 2011, Pages 12680-12691

  Robertson, Alasdair P M ^a   Suter, Riccardo ^a,b   Chabanne, Laurent ^a   Whittell, George R ^a   Manners, Ian ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84055217727     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic201809g     Document Type: Article

References (88)

1. Burkhardt, E. R.; Matos, K. Chem. Rev. 2006, 106, 2617.
2. Kanth, J. V. B. Aldrichimica Acta 2002, 35, 57.
3. Stephens, F. H.; Pons, V.; Baker, R. T. Dalton Trans. 2007, 2613.
4. Staubitz, A.; Robertson, A. P. M.; Manners, I. Chem. Rev. 2010, 110, 4079.
5. Jiang, Y.; Blacque, O.; Fox, T.; Frech, C. M.; Berke, H. Organometallics 2009, 28, 5493.
6. Sloan, M. E.; Staubitz, A.; Lee, K.; Manners, I. Eur. J. Org. Chem. 2011, 672.
7. Staubitz, A.; Soto, A. P.; Manners, I. Angew. Chem., Int. Ed. 2008, 47, 6212.
8. Corso, M.; Auwärter, W.; Muntwiler, M.; Tamai, A.; Greber, T.; Osterwalder, J. Science 2004, 303, 217.
9. Liu, Z.; Song, L.; Zhao, S.; Huang, J.; Ma, L.; Zhang, J.; Lou, J.; Ajayan, P. M. Nano Lett. 2011, 11, 2032.
10. Zhong, B.; Song, L.; Huang, X. X.; Wen, G. W.; Xia, L. Mater. Res. Bull. 2011, 46, 1521.
11. Jaska, C. A.; Temple, K.; Lough, A. J.; Manners, I. J. Am. Chem. Soc. 2003, 125, 9424.
12. Blaquiere, N.; Diallo-Garcia, S.; Gorelsky, S. I.; Black, D. A.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 14034.
13. Friedrich, A.; Drees, M.; Schneider, S. Chem.-Eur. J. 2009, 15, 10339.
14. Käß, M.; Friedrich, A.; Drees, M.; Schneider, S. Angew. Chem., Int. Ed. 2009, 48, 905.
15. Keaton, R. J.; Blacquiere, J. M.; Baker, R. T. J. Am. Chem. Soc. 2007, 129, 1844.
16. Pun, D.; Lobkovsky, E.; Chirik, P. J. Chem. Commun.2007, 3297.
17. Sloan, M. E.; Staubitz, A.; Clark, T. J.; Russell, C. A.; Lloyd Jones, G. C.; Manners, I. J. Am. Chem. Soc. 2010, 132, 3831.
18. Kakizawa, T.; Kawano, Y.; Naganeyama, K.; Shimoi, M. Chem. Lett. 2011, 40, 171.
19. Vance, J. R.; Robertson, A. P.M.; Lee, K.;Manners, I. Chem.-Eur. J. 2011, 17, 4099.
20. Staubitz, A.; Sloan, M. E.; Robertson, A. P. M.; Friedrich, A.; Schneider, S.; Gates, P. J.; Schmedt auf der Günne, J.; Manners, I. J. Am. Chem. Soc. 2010, 132, 13332.
21. Dietrich, B. L.; Goldberg, K. I.; Heinekey, D. M.; Autrey, T.; Linehan, J. C. Inorg. Chem. 2008, 47, 8583.
22. Dallanegra, R.; Robertson, A. P. M.; Chaplin, A. B.; Manners, I.;Weller, A. S. Chem. Commun. 2011, 3763.
23. Zahmakiran, M.; Özkar, S. Inorg. Chem. 2009, 48, 8955.
24. Tang, C. Y.; Thompson, A. L.; Aldridge, S. J. Am. Chem. Soc. 2010, 132, 10578.
25. Shrestha, R. P.; Diyabalanage, H. V. K.; Semelsberger, T. A.; Ott, K. C.; Burrell, A. K. Int. J. Hydrogen Energy 2009, 34, 2616.
26. Hansmann, M. M.; Melen, R. L.; Wright, D. S. Chem. Sci. 2011, 2, 1554.
27. Cowley, H. J.; Holt, M. S.; Melen, R. L.; Rawson, J. M.; Wright, D. S. Chem. Commun. 2011, 2682.
28. Clark, T. J.; Russell, C. A.; Manners, I. J. Am. Chem. Soc. 2006, 128, 9582.
29. Vogt, M.; de Bruin, B.; Berke, H.; Trincado, M.; Grützmacher, H. Chem. Sci., 2011, 2, 723.
30. A catalytic system based upon a metalorganic framework containing active Ni centers has also been reported for ammonia- borane dehydroge nation, although the catalysis in this case occurs in the solid state at 80°C: Li, Y.; Song, P.; Zheng, J.; Li, X. Chem.-Eur. J. 2010, 16, 10887.
31. Kawano, Y.; Uruichi, M.; Shimoi, M.; Taki, S.; Kawaguchi, T.; Kakizawa, T.; Ogino, H. J. Am. Chem. Soc. 2009, 131, 14946.
32. An FeB nanoalloy has also been employed in the catalytic dehydrogenation of ammonia-borane in the solid state at elevated temperatures:He, T.; Wang, J.; Wu, G.; Kim, H.; Proffen, T.; Wu, A.; Li, W.; Liu, T.; Xiong, Z.; Wu, C.; Chu, H.; Guo, J.; Autrey, T.; Zhang, T.; Chen, P. Chem.-Eur. J. 2010, 16, 12814.
33. Miller, A. J. M.; Bercaw, J. E. Chem. Commun. 2010, 1709.
34. Whittell, G. R.; Balmond, E. I.; Robertson, A. P. M.; Patra, S. K.; Haddow, M. F.; Manners, I. Eur. J. Inorg. Chem. 2010, 3967.
35. Chapman, A. M.; Haddow, M. F.; Wass, D. F. J. Am. Chem. Soc. 2011, 133, 8826.
36. Haaland, A. Angew. Chem., Int. Ed. 1989, 28, 992.
37. Göttker-Schnetmann, I.; White, P. S.; Brookhart, M. Organometallics 2004, 23, 1766.
38. Denney, M. C.; Pons, V.; Hebden, T. J.; Heinekey, D. M.; Goldberg, K. I. J. Am. Chem. Soc. 2006, 128, 12048.
39. Clapham, S. E.; Hadzovic, A.; Morris, R. H. Coord. Chem. Rev. 2004, 248, 2201.
40. Li, T.; Churlaud, R.; Lough, A. J.; Abdur-Rashid, K.; Morris, R. H. Organometallics 2004, 23, 6239.
41. Abdur-Rashid, K.; Clapham, S. E.; Hadzovic, A.; Harvey, J. N.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 2002, 124, 15104.
42. Raney, M. Method of Preparing Catalytic Material, U.S. 1563587, 1925.
43. Raney, M. Method of Producing Finely Divided Nickel, U.S. 1628190, 1927.
44. Smith, A. J.; Trimm, D. L. Annu. Rev. Mater. Res. 2005, 35, 127.
45. Fouilloux, P. Appl. Catal. 1983, 8, 1.
46. Ertl, G.; Knozinger, H.; Weitkamp, J. Preparation of Solid Catalysts; Wiley-VCH: Weinheim, Germany, 1999.
47. Jones, W. H.; Benning, W. F.; Davis, P.; Mulvey, D. M.; Pollak, P. I.; Schaeffer, J. C.; Tull, R.; Weinstock, L. M. Ann. N.Y. Acad. Sci. 1969, 158, 471.
48. Onuoha, N. I.;Wainwright, M. S. Chem. Eng. Commun. 1984, 29, 1.
49. Tomsett, A. D.; Wainwright, M. S.; Young, D. J. Appl. Catal. 1984, 12, 43.
50. Ma, L.; Tran, T.; Wainwright, M. S. Top. Catal. 2003, 22, 287.
51. Reeve, W.; Christian, J. J. Am. Chem. Soc. 1956, 78, 860.
52. Johnston, W. D.; Heikes, R. R.; Petrolo, J. J. Am. Chem. Soc. 1957, 79, 5388.
53. Pavlic, A. A.; Adkins, H. J. Am. Chem. Soc. 1946, 68, 1471.
54. Franck-Neumann, M.; Geoffroy, P.; Bissinger, P.; Adelaide, S. Tetrahedron Lett. 2001, 42, 6401.
55. Gallezot, P.; Cerino, P. J.; Blanc, B.; Flèche, G.; Fuertes, P. J. Catal. 1994, 146, 93.
56. Aversa, M. C.; Giannetto, P. J. Chem. Soc. Perkin Trans. 2 1984, 81.
57. Couturier, M.; Tucker, J. L.; Andresen, B. M.; Dubé, P.; Negri, J. T. Org. Lett. 2001, 3, 465.
58. Yao, C. F.; Zhuang, L.; Cao, Y. L.; Ai, X. P.; Yang, H. X. Int. J. Hydrogen Energ. 2008, 33, 2462.
59. The peaks within the 11B NMR spectra were quantified by the addition of a known quantity of B(OiPr)3 to filtered NMR samples (See ref 19) and integrating versus the resulting peak (δB +18 ppm). The borate could not be added directly to the reaction mixture as it was found to interact with skeletal Ni, reducing its dehydrogenation activity. (60) Freel, J.; Pieters, W. J. M.; Anderson, R. B. J. Catal. 1969, 14, 247.
60. Freel, J.; Robertson, S. D.; Anderson, R. B. J. Catal. 1970, 18, 243.
61. Kishida, S.; Teranishi, S. J. Catal. 1968, 12, 90.
62. Widegren, J. A.; Finke, R. G. J. Mol. Catal. A: Chem. 2003, 198, 317.
63. Jaska, C. A.; Manners, I. J. Am. Chem. Soc. 2004, 126, 9776.
64. Widegren, J. A.; Bennett, M. A.; Finke, R. G. J. Am. Chem. Soc. 2003, 125, 10301.
65. Anton, D. R.; Crabtree, R. H. Organometallics 1983, 2, 855.
66. Whitesides, G. M.; Hackett, M.; Brainard, R. L.; Lavalleye, J. P. P. M.; Sowinski, A. F.; Izumi, A. N.; Moore, S. S.; Brown, D. W.; Staudt, E. M. Organometallics 1985, 4, 1819.
67. Stevens, C. J.; Dallanegra, R.; Chaplin, A. B.; Weller, A. S.; MacGregor, S. A.; Ward, B.; McKay, D.; Alcaraz, G.; Sabo-Etienne, S. Chem.-Eur. J. 2011, 17, 3011.
68. Liptrot, D. J.; Hill, M. S.; Mahon, M. F.; MacDougall, D. J. Chem.-Eur. J. 2010, 16, 8508.
69. Chen, Y.; Fulton, J. L.; Linehan, J. C.; Autrey, T. J. Am. Chem. Soc. 2005, 127, 3254.
70. Pons, V.; Baker, R. T.; Szymczak, N. K.; Heldebrant, D. J.; Linehan, J. C.; Matus, M. H.; Grant, D. J.; Dixon, D. A. Chem. Commun. 2008, 6597.
71. Paul, A.; Musgrave, C. B. Angew. Chem., Int. Ed. 2007, 46, 8153.
72. Yang, X.; Hall, M. B. J. Am. Chem. Soc. 2008, 130, 1798.
73. Zimmerman, P. M.; Paul, A.; Zhang, Z.; Musgrave, C. B. Angew. Chem. Int Ed. 2009, 48, 2201.
74. Ryschkewitsch, G. E.; Wiggins, J. W. Inorg. Chem. 1970, 9, 314.
75. Douglas, T. M.; Chaplin, A. B.; Weller, A. S.; Yang, X.; Hall, M. B. J. Am. Chem. Soc. 2009, 131, 15440.
76. Luo, Y.; Ohno, K. Organometallics 2007, 26, 3597.
77. Nöth, H.; Thomas, S. Eur. J. Inorg. Chem. 1999, 1373.
78. Pasumansky, L.; Haddenham, D.; Clary, J. W.; Fisher, G. B.; Goralski, C. T.; Singaram, B. J. Org. Chem. 2008, 73, 1898.
79. Baldwin, R. A.; Washburn, R. M. J. Org. Chem. 1961, 26, 3549.
80. Brown, H. C.; Schlesinger, H. I.; Cardon, S. Z. J. Am. Chem. Soc. 1942, 64, 325.
81. Jaska, C. A.; Clark, T. J.; Clendenning, S. B.; Grozea, D.; Turak, A.; Lu, Z.-H.; Manners, I. J. Am. Chem. Soc. 2005, 127, 5116.
82. Flores-Segura, H.; Torres, L. A. Struct. Chem. 1997, 8, 227.
83. Staubitz, A.; Besora, M.; Harvey, J. N.; Manners, I. Inorg. Chem. 2008, 47, 5910.
84. Jaska, C. A.; Temple, K.; Lough, A. J.; Manners, I. Chem. Commun. 2001, 962.
85. Dallanegra, R.; Chaplin, A. B.; Tsim, J.; Weller, A. S. Chem. Commun. 2010, 3092.
86. Smythe, N. C.; Gordon, J. C. Eur. J. Inorg. Chem. 2010, 509.
87. This peak, based on integration versus the remaining peaks of the trimer, may potentially also contain some contribution from its isomeric form, [NH.2 BH.2]3, which has been reported at an almost identical similar chemical shift: Shaw, W. J.; Linehan, J. C.; Szymczak, N. K.; Heldebrant, D. J.; Yonker, C.; Camaioni, D. M.; Baker, R. T.; Autrey, T. Angew. Chem., Int. Ed. 2008, 47, 7493
88. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518.