Citation: Zhao Qianyi, Liang Yuan, Xu Ting, Dou Ting, Zhang Jie, Chen Xuenian. Synthesis of Osmium Complexes with Bidentate Nitrogen-Based Ligands and Their Application in Catalytic Dehydrogenation of Ammonia Borane[J]. Chinese Journal of Organic Chemistry, ;2018, 38(12): 3286-3295. doi: 10.6023/cjoc201805050 shu

Synthesis of Osmium Complexes with Bidentate Nitrogen-Based Ligands and Their Application in Catalytic Dehydrogenation of Ammonia Borane

School of Chemistry and Chemical Engineering, Henan Key Laboratory of Boron Chemistry and Advanced Energy Materials, Henan Normal University, Xinxiang 453007

Corresponding author: Zhao Qianyi, qyzhao@htu.edu.cn Chen Xuenian, xnchen@htu.edu.cn
Received Date: 28 May 2018
Revised Date: 10 July 2018
Available Online: 14 December 2018
Fund Project: the National Natural Science Foundation of China 21503070the National Natural Science Foundation of China 21501048the National Natural Science Foundation of China 21571052the Key Science and Technology Project of Henan Province 182102210377the National Natural Science Foundation of China 21771057Project supported by the National Natural Science Foundation of China (Nos. 21501048, 21503070, 21571052, 21771057) and the Key Science and Technology Project of Henan Province (No.182102210377)

Figures(7)

Reactions of OsCl₂(PPh₃)₃ (1) with bidentate nitrogen-based ligands at room temperature led to the formation of complexes OsCl₂(PPh₃)₂(diamine) (2~6) and OsCl₂(PPh₃)₂(Phen^*) (7~11). Complexes 2~11 showed high activity in the catalytic dehydrogenation of ammonia borane at 60℃, in THF/DME (V:V=1:1.6) solution with the catalyst loading of 5 mol%. Among all the catalysts, compound 4 demonstrated the highest catalytic activity, which represents the most efficient osmium catalyst in catalytic dehydrogenation of ammonia borane until now.
- osmium,
- complex,
- synthesis,
- catalytic dehydrogenation,
- ammonia borane
1. [1]
  Rand, D. A. J.; Dell, R. M. Hydrogen Energy: Challenges and Prospects, Royal Society of Chemistry, Cambridge, UK, 2008.
2. [2]
  (a) Yadav, M.; Xu, Q. Energy Environ. Sci. 2012, 5, 9698.
  (b) Dalebrook, A. F.; Gan, W.; Grasemann, M.; Moret, S.; Laurenczy, G. Chem. Commun. 2013, 49, 8735.
3. [3]
  (a) Staubitz, A.; Robertson, A. P. M.; Manners, I. Chem. Rev. 2010, 110, 4079.
  (b) Zhang, X.; Kam, L.; Trerise, R.; Williams, T. J. Acc. Chem. Res. 2017, 50, 86.
4. [4]
  (a) Tang, Z.; Chen, X.; Chen, H.; Wu, L.; Yu, X. Angew. Chem., Int. Ed. 2013, 52, 5832.
  (b) Tang, Z.; Chen, H.; Chen, X.; Wu, L.; Yu, X. J. Am. Chem. Soc. 2012, 134, 5464.
5. [5]
  Wang, K.; Zhang, J.-G.; Man, T.-T.; Wu, M.; Chen, C.-C. Chem.-Asian. J. 2013, 8, 1076. doi: 10.1002/asia.201201241
6. [6]
  (a) Appelt, C.; Chris Slootweg, J.; Lammertsma, K.; Uhl, W. Angew. Chem., Int. Ed. 2013, 52, 4256.
  (b) Kalidindi, S. B.; Joseph, J.; Jagirdar, B. R. Energ. Environ. Sci. 2009, 2, 1274.
7. [7]
  (a) Alcaraz, G.; Sabo-Etienne, S. Angew. Chem., Int. Ed. 2010, 49, 7170.
  (b) Staubitz, A.; Robertson, A. P. M.; Sloan, M. E.; Manners, I. Chem. Rev. 2010, 110, 4023.
  (c) Rossin, A.; Peruzzini, M. Chem. Rev. 2016, 116, 8848.
8. [8]
  (a) Esteruelas, M. A.; López, A. M.; Mora, M. ACS Catal. 2015, 5, 187; (b) Esteruelas, M. A.; Fernández, I.; López, A. M. Organometallics 2014, 33, 1104.
9. [9]
  (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
  (b) Döbler, C.; Mehltretter, G. M.; Sundermeier, U.; Beller, M. J. Am. Chem. Soc. 2000, 122, 10289.
  (c) Döbler, C.; Mehltretter, G. M.; Sundermeier, U.; Beller, M. J. Organomet. Chem. 2001, 621, 70. (d) Heravi, M. M.; Zadsirjan, V.; Esfandyari, M.; Lashaki, T. B. Tetrahedron: Asymmetry 2017, 28, 987.
10. [10]
  (a) Esteruelas, M. A.; Honczek, N.; Oliván, M.; Onate, E.; Valencia, M. Organometallics 2011, 30, 2468.
  (b) Bertoli, M.; Choualeb, A.; Lough, A. J.; Moore, B.; Spasyuk, D.; Gusev, D. G. Organometallics 2011, 30, 3479.
  (c) Buil, M. L.; Esteruelas, M. A.; Herrero, J.; Izquierdo, S.; Pastor, I. M.; Yus, M. ACS Catal. 2013, 3, 2072.
  (d) Chelucci, G.; Baldino, S.; Baratta, W. Acc. Chem. Res. 2015, 48, 363.
  (e) Bolaño, T.; Esteruelas, M. A.; Gay, M. P.; Oñate, E.; Pastor, I. M.; Yus, M. Organometallics 2015, 34, 3902.
  (f) Barbato, C.; Baldino, S.; Ballico, M.; Figliolia, M.; Magnolia, S.; Siega, K.; Herdtweck, E.; Strazzolini, P.; Chelucci, G.; Baratta, W. Organometallics 2018, 37, 65..
11. [11]
  Spasyuk, D.; Vicent, C.; Gusev, D. G. J. Am. Chem. Soc. 2015, 137, 3743. doi: 10.1021/ja512389y
12. [12]
  Buil, M. L.; Esteruelas, M. A.; Gay, M. P. Organometallics 2018, 37, 603. doi: 10.1021/acs.organomet.7b00906
13. [13]
  (a) Baratta, W.; Bossi, G.; Putignano, E.; Rigo, P. Chem.-Eur. J. 2011, 17, 3474.
  (b) Chelucci, G.; Baldino, S.; Baratta, W. Coord. Chem. Rev. 2015, 300, 29.
14. [14]
  Baker, R. T.; Gordon, J. C.; Hamilton, C. W. J. Am. Chem. Soc. 2012, 134, 5598. doi: 10.1021/ja210542r
15. [15]
  When the article was prepared, a similar synthetic method for complex 2 was reported by Baratta. Please see Ref.[10f] for details.
16. [16]
  Nascimento, R. D.; Silva, A. K.; Lião, L. M. J. Mol. Struct. 2018, 1151, 277. doi: 10.1016/j.molstruc.2017.09.044
17. [17]
  Hoffman, P. R.; Caulton, K. G. J. Am. Chem. Soc. 1975, 97, 4221. doi: 10.1021/ja00848a012
18. [18]
  (a) Lay, P. A.; Sargeson, A. M.; Skelton, B, W. J. Am. Chem. Soc. 1982, 104, 6161.
  (b) Clapham, S. E.; Morris, R. H. Organometallics 2005, 24, 479.
  (c) McQueen, J. S.; Nagao, N.; Eberspacher, T. Inorg. Chem. 2003, 42, 3815.
  (d) Ettner, N.; Hillen, W.; Ellestad, G. A. J. Am. Chem. Soc. 1993, 115, 2546.
  (e) Peacock, A. F. A.; Habtemariam, A.; Moggach, S. A. Inorg. Chem. 2007, 46, 4049.
  (f) Gong, L.; Lin, Y.; Wen, T. B. Organometallics 2009, 28, 1101.
  (g) Martínez-Peña, F.; Pizarro, A. M. Chem.-Eur. J. 2017, 23, 16231.
19. [19]
  Luman, C. R.; Castellano, F. N. In Comprehensive Coordination Chemistry Ⅱ, 2nd ed., Vol. 1, Eds.: Meyer, T. J.; McCleverty, J. A., Elsevier Ltd., Pergamon, 2003, p. 25.
20. [20]
  (a) Akerboom, S.; van den Elshout, J. J. M. H.; Mutikainen, I. Eur. J. Inorg. Chem. 2013, 2013, 6137.
  (b) Nakagawa, A.; Ito, A.; Sakuda, E. Eur. J. Inorg. Chem. 2017, 3794.
  (c) Glazer, E. C.; Magde, D.; Tor, Y. J. Am. Chem. Soc. 2007, 129, 8544.
21. [21]
  Sjögren, M. P. T.; Frisell, H. B. Organometallics 1997, 16, 942. doi: 10.1021/om960260i
22. [22]
  (a) Zheng, A.-X.; Si, J.; Tang, X.-Y.; Miao, L.-L.; Yu, M.; Hou, K.-P.; Wang, F.; Li, H.-X.; Lang, J.-P. Inorg. Chem. 2012, 51, 10262.
  (b) Zheng, A.-X.; Wang, H.-F.; Lü, C.-N.; Ren, Z.-G.; Li, H.-X.; Lang, J.-P. Dalton Trans. 2012, 41, 558.
  (c) Li, F.-L.; Yang, S.-P.; Zhang, W.-H.; Liu, Q.; Yu, H.; Chen, J.-X.; Lang, J.-P. ChemistrySelect 2016, 1, 2979.
23. [23]
  (a) Liu, B.; Zhao, Q.; Wang, H. Chin. J. Chem. 2012, 30, 2158.
  (b) Nakamura, A.; Sato, T.; Kuroda, R. Chem. Commun. 2004, 2858.
  (c) Carlson, B.; Phelan, G. D.; Kaminsky, W. J. Am. Chem. Soc. 2002, 124, 14162.
  (d) Cheng, Y. K.; Cheung, J.; Che, K.-K.; Chi, M. Chem. Commun. 1997, 623.
  (e) Carlson, B.; Phelan, G. D.; Benedict, J. B. Inorg. Chim. Acta 2006, 359, 1093.
24. [24]
  Bhattacharya, P.; Krause, J. A.; Guan, H. J. Am. Chem. Soc. 2014, 136, 11153. doi: 10.1021/ja5058423
25. [25]
  Duman, S.; Özkar, S. Int. J. Hydrogen Energy 2013, 38, 180. doi: 10.1016/j.ijhydene.2012.10.041
26. [26]
  (a) Rossin, A.; Rossi, A.; Peruzzini, M. ChemPlusChem 2014, 79, 1316.
  (b) Metters, O. J.; Chapman, A. M.; Robertson, A. P. M.; Woodall, C. H.; Gates, P. J.; Wass, D. F.; Manners, I. Chem. Commun. 2014, 50, 12146.
  (c) Robertson, A. P. M.; Leitao, E. M.; Jurca, T.; Haddow, M. F.; Helten, H.; Lloyd-Jones, G. C.; Manners, I. J. Am. Chem. Soc. 2013, 135, 12670.
  (d) Pons, V.; Baker, R. T. Angew. Chem., Int. Ed. 2008, 47, 9600.
  (e) Staubitz, A.; Presa Soto, A.; Manners, I. Angew. Chem., Int. Ed. 2008, 47, 6212.
27. [27]
  (a) Kalviri, H. A.; Gärtner, F.; Ye, G. Chem. Sci. 2015, 6, 618. (b) Shaw, W. J.; Linehan, J. C.; Szymczak, N. K. Angew. Chem., Int. Ed. 2008, 47, 7493.
28. [28]
  Sayalero, S.; Pericas, M. A. Synlett 2006, 2585.
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