Articles

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

  • Zhao Qianyi ,
  • Liang Yuan ,
  • Xu Ting ,
  • Dou Ting ,
  • Zhang Jie ,
  • Chen Xuenian
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  • School of Chemistry and Chemical Engineering, Henan Key Laboratory of Boron Chemistry and Advanced Energy Materials, Henan Normal University, Xinxiang 453007

Received date: 2018-05-28

  Revised date: 2018-07-10

  Online published: 2018-08-14

Supported by

Project 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).

Abstract

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.

Cite this article

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

References

[1] Rand, D. A. J.; Dell, R. M. Hydrogen Energy:Challenges and Prospects, Royal Society of Chemistry, Cambridge, UK, 2008.
[2] (a) Yadav, M.; Xu, Q. Energy Environ. Sci. 2012, 5, 9698.
(b) Dalebrook, A. F.; Gan, W.; Grasemann, M.; Moret, S.; Lau-renczy, G. Chem. Commun. 2013, 49, 8735.
[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] (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] Wang, K.; Zhang, J.-G.; Man, T.-T.; Wu, M.; Chen, C.-C. Chem.-Asian. J. 2013, 8, 1076.
[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] (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] (a) Esteruelas, M. A.; López, A. M.; Mora, M. ACS Catal. 2015, 5, 187;
(b) Esteruelas, M. A.; Fernández, I.; López, A. M. Organo-metallics 2014, 33, 1104.
[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] (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] Spasyuk, D.; Vicent, C.; Gusev, D. G. J. Am. Chem. Soc. 2015, 137, 3743.
[12] Buil, M. L.; Esteruelas, M. A.; Gay, M. P. Organometallics 2018, 37, 603.
[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] Baker, R. T.; Gordon, J. C.; Hamilton, C. W. J. Am. Chem. Soc. 2012, 134, 5598.
[15] When the article was prepared, a similar synthetic method for complex 2 was reported by Baratta. Please see Ref.[10f] for details.
[16] Nascimento, R. D.; Silva, A. K.; Lião, L. M. J. Mol. Struct. 2018, 1151, 277.
[17] Hoffman, P. R.; Caulton, K. G. J. Am. Chem. Soc. 1975, 97, 4221.
[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] 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] (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] Sjögren, M. P. T.; Frisell, H. B. Organometallics 1997, 16, 942.
[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] (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] Bhattacharya, P.; Krause, J. A.; Guan, H. J. Am. Chem. Soc. 2014, 136, 11153.
[25] Duman, S.; Özkar, S. Int. J. Hydrogen Energy 2013, 38, 180.
[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] (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] Sayalero, S.; Pericas, M. A. Synlett 2006, 2585.

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