Reduction of borazines mediated by low-valent chromium species

Angewandte Chemie - International Edition

Volumn 51, Issue 52, 2012, Pages 13168-13172

  Carter, Tyler J ^a   Kampf, Jeff W ^a   Szymczak, Nathaniel K ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

Amine boranes; Borazines; Chromium; Hydrogen storage; Reduction

Indexed keywords

AMINE-BORANES; BORAZINE; BORAZINES; CHROMIUM SPECIES; HYDRIDE TRANSFERS; HYDROGENATION PATHWAY; LOW-VALENT; METAL HYDRIDES; PROTON DONORS; REDUCTANTS; REGENERATION STRATEGIES;

ADDITION REACTIONS; BORON COMPOUNDS; HYDRIDES; HYDROGEN STORAGE; HYDROGENATION; METAL COMPLEXES; OLEFINS; PROTONATION; REDUCTION; SPENT FUELS;

CHROMIUM;

EID: 84872004949     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201206668     Document Type: Article

References (55)

1. U.S. Department of Energy, "Targets for Onboard Hydrogen Storage Systems for Light-Duty Vehicles", can be found under http://www1.eere. energy.gov/hydrogenandfuelcells/storage/ pdfs/targets-onboard-hydro-storage- explanation.pdf, 2009.
2. A. Staubitz, A. P. M. Robertson, I. Manners, Chem. Rev. 2010, 110, 4079
3. N. C. Smythe, J. C. Gordon, Eur. J. Inorg. Chem. 2010, 509
4. F. H. Stephens, V. Pons, R. T. Baker, Dalton Trans. 2007, 2613.
5. C. A. Jaska, K. Temple, A. J. Lough, I. Manners, Chem. Commun. 2001, 962
6. A. Gutowska, L. Li, Y. Shin, C. M.Wang, X. S. Li, J. C. Linehan, R. S. Smith, B. D. Kay, B. Schmid, W. Shaw, M. Gutowski, T. Autrey, Angew. Chem. 2005, 117, 3644
7. Angew. Chem. Int. Ed. 2005, 44, 3578
8. M. E. Bluhm, M. G. Bradley, R. Butterick III, U. Kusari, L. G. Sneddon, J. Am. Chem. Soc. 2006, 128, 7748
9. M. C. Denney, V. Pons, T. J. Hebden, D. M. Heinekey, K. I. Goldberg, J. Am. Chem. Soc. 2006, 128, 12048
10. R. J. Keaton, J. M. Blacquiere, R. T. Baker, J. Am. Chem. Soc. 2007, 129, 1844
11. J. M. Yan, X. B. Zhang, S. Han, H. Shioyama, Q. Xu, Angew. Chem. 2008, 120, 2319
12. Angew. Chem. Int. Ed. 2008, 47, 2287
13. D.W. Himmelberger, C.W. Yoon, M. E. Bluhm, P. J. Carroll, L. G. Sneddon, J. Am. Chem. Soc. 2009, 131, 14101
14. M. Käß, A. Friedrich, M. Drees, S. Schneider, Angew. Chem. 2009, 121, 922
15. Angew. Chem. Int. Ed. 2009, 48, 905.
16. P. V. Ramachandran, P. D. Gagare, Inorg. Chem. 2007, 46, 7810
17. S. Hausdorf, F. Baitalow, G. Wolf, F. O. R. L. Mertens, Int. J. Hydrogen Energy 2008, 33, 608
18. A. D. Sutton, A. K. Burrell, D. A. Dixon, E. B. Garner III, J. C. Gordon, T. Nakagawa, K. C. Ott, J. P. Robinson, M. Vasiliu, Science 2011, 331, 1426
19. B. L. Davis, D. A. Dixon, E. B. Garner, J. C. Gordon, M. H. Matus, B. Scott, F. H. Stephens, Angew. Chem. 2009, 121, 6944
20. Angew. Chem. Int. Ed. 2009, 48, 6812
21. P. G. Campbell, L. N. Zakharov, D. J. Grant,D. A. Dixon, S. Y. Liu, J. Am. Chem. Soc. 2010, 132, 3289
22. M. T. Mock, R. G. Potter, D. M. Camaioni, J. Li, W. G. Dougherty, W. S. Kassel, B. Twamley, D. L. DuBois, J. Am. Chem. Soc. 2009, 131, 14454.
23. M. H. Matus, K. D. Anderson, D. M. Camaioni, S. T. Autrey, D. A. Dixon, J. Phys. Chem. A 2007, 111, 4411, and references therein.
24. W. R. Nutt, M. L. McKee, Inorg. Chem. 2007, 46, 7633.
25. Borazines are known to be one of the products of amine-borane dehydrocoupling: C. A. Jaska, K. Temple, A. J. Lough, I. Manners, J. Am. Chem. Soc. 2003, 125, 9424
26. R. P. Shrestha, H. V. K. Diyabalanage, T. A. Semelsberger, K. C. Ott, A. K. Burrell, Int. J. Hydrogen Energy 2009, 34, 2616
27. W. J. Shaw, J. C. Linehan, N. K. Szymczak, D. J. Heldebrant, C. Yonker, D. M. Camaioni, R. T. Baker, T. Autrey, Angew. Chem. 2008, 120, 7603
28. Angew. Chem. Int. Ed. 2008, 47, 7493
29. J. F. Kostka, R. Schellenberg, F. Baitalow, T. Smolinka, F. Mertens, Eur. J. Inorg. Chem. 2012, 49.
30. J. P. Djukic, F. Rose-Munch, E. Rose, Y. Dromzee, J. Am. Chem. Soc. 1993, 115, 6434
31. E. P. Kuendig, D. Amurrio, G. Bernardinelli, R. Chowdhury, Organometallics 1993, 12, 4275.
32. A. Staubitz, M. Besora, J. N. Harvey, I. Manners, Inorg. Chem. 2008, 47, 5910.
33. R. Prinz, H. Werner, Angew. Chem. 1967, 79, 63
34. Angew. Chem. Int. Ed. Engl. 1967, 6, 91
35. H. Werner, R. Prinz, E. Deckelmann, Chem. Ber. 1969, 102, 95
36. K. Deckelmann, H. Werner, Helv. Chim. Acta 1970, 53, 139
37. M. Scotti, H.Werner, Helv. Chim. Acta 1974, 57, 1234
38. M. Scotti, H. Werner, J. Organomet. Chem. 1974, 81, C17.
39. G. Huttner, B. Krieg, Angew. Chem. 1971, 83, 541
40. Angew. Chem. Int. Ed. Engl. 1971, 10, 512.
41. E. Deckelmann, H. Werner, Helv. Chim. Acta 1969, 52, 892
42. M. Scotti, H. Werner, D. L. S. Brown, S. Cavell, J. A. Connor, H. A. Skinner, Inorg. Chim. Acta 1977, 25, 261.
43. Direct reduction of a derivative of an alternative H2-storage material related to 1,2-dihydro-1,2-azaborine was recently reported to occur with both KH/HCl and H2 with Pd/C. See Ref. [4e] for more details.
44. Borazine reduction with alkyl nucleophiles has been observed by Nçth and co-workers. For representative examples, see: H. Nçth, A. Troll, Eur. J. Inorg. Chem. 2005, 3524
45. H. Nçth, S. Rojas-Lima, A. Troll, Eur. J. Inorg. Chem. 2005, 1895.
46. R. Islas, E. Chamorro, J. Robles, T. Heine, J. C. Santos, G. Merino, Struct. Chem. 2007, 18, 833.
47. Compound 2 is thermally sensitive and decomposes readily at room temperature
48. however, the reaction mixture may be stored in the freezer for up to five days without significant decomposition. Species 2 can be observed in solutions of the reaction mixture by low-temperature (-208C) NMR spectroscopy.
49. A. S. Lisovenko, A. Y. Timoshkin, Inorg. Chem. 2010, 49, 10357.
50. S. G. Shore, C. W. Hickam, Inorg. Chem. 1963, 2, 638
51. G. H. Dahl, R. Schaeffer, J. Am. Chem. Soc. 1961, 83, 3032.
52. Studies used DOAcF to aid spectroscopic analyses. Note that control reactions using HOAcF proceeded identically (see the Supporting Information).
53. Assigned by comparison to the reaction with HOAcF, which has bands at 3233 and 3207 cm-1.
54. J. L. Adcock, J. J. Lagowski, Inorg. Chem. 1973, 12, 2533
55. J. J. Lagowski, Coord. Chem. Rev. 1977, 22, 185.