Accessing zinc monohydride cations through coordinative interactions

Angewandte Chemie - International Edition

Volumn 53, Issue 35, 2014, Pages 9347-9351

  Lummis, Paul A ^a   Momeni, Mohammad R ^a   Lui, Melanie W ^a   McDonald, Robert ^a   Ferguson, Michael J ^a   Miskolzie, Mark ^a   Brown, Alex ^a   Rivard, Eric ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

cations; homogeneous catalysis; hydrides; N heterocyclic carbene; zinc

Indexed keywords

CATALYSIS; COMPUTATIONAL METHODS; HYDRIDES; HYDROSILYLATION; POSITIVE IONS; REACTION KINETICS; ZINC;

HOMOGENEOUS CATALYSIS; N-HETEROCYCLIC CARBENES;

ORGANIC COMPOUNDS;

EID: 84915824919     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201404611     Document Type: Article

References (52)

1. A. E. Finholt, A. C. Bond, Jr., H. I. Schlesinger, J. Am. Chem. Soc. 1947, 69, 1199
2. J. J. Watkins, E. C. Ashby, Inorg. Chem. 1974, 13, 2350
3. for the synthesis of gas-phase ZnH2, see:, A. Shayesteh, S. Yu, P. F. Bernath, Chem. Eur. J. 2005, 11, 4709.
4. C. Deutsch, N. Krause, B. H. Lipshutz, Chem. Rev. 2008, 108, 2916
5. C. Boone, I. Korobkov, G. I. Nikonov, ACS Catal. 2013, 3, 2336, and references therein
6. F. Alonso, P. Riente, M. Yus, Acc. Chem. Res. 2011, 44, 379
7. T. Vergote, F. Nahra, A. Merschaert, O. Riant, D. Peeters, T. Leyssens, Organometallics 2014, 33, 1953.
8. N. A. Bell, P. T. Moseley, H. M. M. Shearer, C. B. Spencer, J. Chem. Soc. Chem. Commun. 1980, 359
9. A. Looney, R. Han, I. B. Gorrell, M. Cornebise, K. Yoon, G. Parkin, A. L. Rheingold, Organometallics 1995, 14, 274
10. M. Krieger, B. Neumüller, K. Dehnicke, Z. Anorg. Allg. Chem. 1998, 624, 1563
11. H. Hao, C. Cui, H. W. Roesky, G. Bai, H. G. Schmidt, M. Noltemeyer, Chem. Commun. 2001, 1118
12. Z. Zhu, R. J. Wright, M. M. Olmstead, E. Rivard, M. Brynda, P. P. Power, Angew. Chem. 2006, 118, 5939
13. Angew. Chem. Int. Ed. 2006, 45, 5807
14. W. Marciniak, K. Merz, M. Moreno, M. Driess, Organometallics 2006, 25, 4931
15. M. P. Coles, S. M. El-Hamruni, J. D. Smith, P. B. Hitchcock, Angew. Chem. 2008, 120, 10301
16. Angew. Chem. Int. Ed. 2008, 47, 10147
17. J. Spielmann, D. Piesik, B. Wittkamp, G. Jansen, S. Harder, Chem. Commun. 2009, 3455
18. I. L. Fedushkin, O. V. Eremenko, A. A. Skatova, A. V. Piskunov, G. K. Fukin, S. Yu. Ketkov, E. Irran, H. Schumann, Organometallics 2009, 28, 3863
19. D. Mukherjee, A. Ellern, A. D. Sadow, J. Am. Chem. Soc. 2010, 132, 7582
20. G. Bendt, S. Schultz, J. Spielmann, S. Schmidt, D. Bläser, C. Wölper, Eur. J. Inorg. Chem. 2012, 3725
21. A. Rit, T. P. Spaniol, L. Maron, J. Okuda, Organometallics 2014, 33, 2039.
22. P. Jochmann, D. W. Stephan, Angew. Chem. 2013, 125, 10014
23. Angew. Chem. Int. Ed. 2013, 52, 9831
24. W. Sattler, G. Parkin, J. Am. Chem. Soc. 2011, 133, 9708
25. W. Sattler, G. Parkin, J. Am. Chem. Soc. 2012, 134, 17462
26. N. J. Brown, J. E. Harris, X. Yin, I. Silverwood, A. J. P. White, S. G. Kazarian, K. Hellgardt, M. S. P. Shaffer, C. K. Williams, Organometallics 2014, 33, 1112.
27. A. Rit, T. P. Spaniol, L. Maron, J. Okuda, Angew. Chem. 2013, 125, 4762
28. Angew. Chem. Int. Ed. 2013, 52, 4664.
29. ZnH+ has been identified at 4K:, M. Kajita, M. Abe, M. Hada, Y. Moriwaki, J. Phys. B 2011, 44, 025402.
30. S. M. I. Al-Rafia, P. A. Lummis, A. K. Swarnakar, K. C. Deutsch, M. J. Ferguson, R. McDonald, E. Rivard, Aust. J. Chem. 2013, 66, 1235.
31. K. C. Thimer, S. M. I. Al-Rafia, M. J. Ferguson, R. McDonald, E. Rivard, Chem. Commun. 2009, 7119
32. S. M. I. Al-Rafia, A. C. Malcolm, S. K. Liew, M. J. Ferguson, E. Rivard, J. Am. Chem. Soc. 2011, 133, 777
33. S. M. I. Al-Rafia, A. C. Malcolm, R. McDonald, M. J. Ferguson, E. Rivard, Angew. Chem. 2011, 123, 8504
34. Angew. Chem. Int. Ed. 2011, 50, 8354
35. S. M. I. Al-Rafia, A. C. Malcolm, R. McDonald, M. J. Ferguson, E. Rivard, Chem. Commun. 2012, 48, 1308
36. S. M. I. Al-Rafia, M. R. Momeni, M. J. Ferguson, R. McDonald, A. Brown, E. Rivard, Organometallics 2013, 32, 6658.
37. For the use of Li[HBsBu3] as a mild source of hydride, see:, A. F. Richards, A. D. Phillips, M. M. Olmstead, P. P. Power, J. Am. Chem. Soc. 2003, 125, 3204.
38. For full synthetic, crystallographic and computational details see the Supporting Information. CCDC997530 (2), 997531 (3), 997532 (4), and 997533 (5) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
39. A. R. Waldeck, P. W. Kuchel, A. J. Lennon, B. E. Chapman, Prog. Nucl. Magn. Reson. Spectrosc. 1997, 30, 39. The diffusion coefficients of 2 and ImMe2iPr2?ZnEt2 were determined to be 8.9×10-10 and 1.2×10-9m2 s -1 respectively in [D8]-THF, and 7.4×10 -10 and 9.8×10-10m2 s-1 respectively in [D8]toluene.
40. H. J. Bestmann, O. Kratzer, Chem. Ber. 1963, 96, 1899.
41. S. M. I. Al-Rafia, A. C. Malcolm, S. K. Liew, M. J. Ferguson, R. McDonald, E. Rivard, Chem. Commun. 2011, 47, 6987.
42. R. W. Alder, P. R. Allen, M. Murray, A. G. Orpen, Angew. Chem. 1996, 108, 1211
43. Angew. Chem. Int. Ed. Engl. 1996, 35, 1121.
44. M. Ma, A. Sidiropoulos, L. Ralte, A. Stasch, C. Jones, Chem. Commun. 2013, 49, 48.
45. S. Pelz, M. Mohr, Organometallics 2011, 30, 383.
46. D. L. Reger, S. S. Mason, A. L. Rheingold, J. Am. Chem. Soc. 1993, 115, 10406
47. Z. Zhu, M. Brynda, R. J. Wright, R. C. Fischer, W. A. Merrill, E. Rivard, R. Wolf, J. C. Fettinger, M. M. Olmstead, P. P. Power, J. Am. Chem. Soc. 2007, 129, 10847
48. Z. Zhu, J. C. Fettinger, M. M. Olmstead, P. P. Power, Organometallics 2009, 28, 2091.
49. For the synthesis of the metal hydride cation [IPr?Cu(μ-H)Cu?IPr] + by an alternate route, see:, C. M. Wyss, B. K. Tate, J. Basca, T. G. Gray, J. P. Sadighi, Angew. Chem. 2013, 125, 13158
50. Angew. Chem. Int. Ed. 2013, 52, 12920.
51. D. Wang, K. Wurst, M. R. Buchmeiser, J. Organomet. Chem. 2004, 689, 2123.
52. S. Enthaler, ACS Catal. 2013, 3, 150.