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

  • 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.
  • 加载中
    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.
       

  • 加载中
    1. [1]

      Qilu DU , Li ZHAO , Peng NIE , Bo XU . Synthesis and characterization of osmium-germyl complexes stabilized by triphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1088-1094. doi: 10.11862/CJIC.20240006

    2. [2]

      Chenyang WANG , Yiyan BAI , Wei ZHANG , Zhaorong LIU , Yuchun WANG . Performance of photo-assisted copper oxide catalyzed hydrolysis of ammonia borane to produce hydrogen. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 97-110. doi: 10.11862/CJIC.20250116

    3. [3]

      Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145

    4. [4]

      Jiaming Xu ,  Yu Xiang ,  Weisheng Lin ,  Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093

    5. [5]

      Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278

    6. [6]

      Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012

    7. [7]

      Ying Chen ,  Ronghua Yan ,  Weiyan Yin . Research Progress on the Synthesis of Metal Single-Atom Catalysts and Their Applications in Electrocatalytic Hydrogen Evolution Reactions. University Chemistry, 2025, 40(9): 344-353. doi: 10.12461/PKU.DXHX202503066

    8. [8]

      Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . Research Progress on Carbon-based Catalysts for Catalytic Dehydrogenation of Liquid Organic Hydrogen Carriers. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-0. doi: 10.1016/j.actphy.2024.100044

    9. [9]

      Xuyu WANG , Xinran XIE , Dengke CAO . Photoreaction characteristics and luminescence modulation in phosphine-anthracene-based Au(Ⅰ) and Ir(Ⅲ) complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1513-1522. doi: 10.11862/CJIC.20250113

    10. [10]

      Xiaotong LU , Pan ZHANG , Zijie ZHAO , Lei HUANG , Hongwei ZUO , Lili LIANG . Antitumor and antibacterial activities of pyridyl Schiff base indium and dysprosium complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1523-1532. doi: 10.11862/CJIC.20250073

    11. [11]

      Zuozhong Liang ,  Lingling Wei ,  Yiwen Cao ,  Yunhan Wei ,  Haimei Shi ,  Haoquan Zheng ,  Shengli Gao . Exploring the Development of Undergraduate Scientific Research Ability in Basic Course Instruction: A Case Study of Alkali and Alkaline Earth Metal Complexes in Inorganic Chemistry. University Chemistry, 2024, 39(7): 247-263. doi: 10.3866/PKU.DXHX202310103

    12. [12]

      Xinyi Zhang , Kai Ren , Yanning Liu , Zhenyi Gu , Zhixiong Huang , Shuohang Zheng , Xiaotong Wang , Jinzhi Guo , Igor V. Zatovsky , Junming Cao , Xinglong Wu . Progress on Entropy Production Engineering for Electrochemical Catalysis. Acta Physico-Chimica Sinica, 2024, 40(7): 2307057-0. doi: 10.3866/PKU.WHXB202307057

    13. [13]

      Lixing ZHANG , Yaowen WANG , Xu HAN , Junhong ZHOU , Jinghui WANG , Liping LI , Guangshe LI . Research progress in the synthesis of fluorine-containing perovskites and their derivatives. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1689-1701. doi: 10.11862/CJIC.20250007

    14. [14]

      Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428

    15. [15]

      Lei Feng , Ze-Min Zhu , Ying Yang , Zongbin He , Jiafeng Zou , Man-Bo Li , Yan Zhao , Zhikun Wu . Long-Pursued Structure of Au23(S-Adm)16 and the Unexpected Doping Effects. Acta Physico-Chimica Sinica, 2024, 40(5): 2305029-0. doi: 10.3866/PKU.WHXB202305029

    16. [16]

      Chunling Qin , Shuang Chen , Hassanien Gomaa , Mohamed A. Shenashen , Sherif A. El-Safty , Qian Liu , Cuihua An , Xijun Liu , Qibo Deng , Ning Hu . Regulating HER and OER Performances of 2D Materials by the External Physical Fields. Acta Physico-Chimica Sinica, 2024, 40(9): 2307059-0. doi: 10.3866/PKU.WHXB202307059

    17. [17]

      Qing ZHANG , Kexin ZHOU , Yanjun GUO , Guangjun CHEN , Bai HE , Bo YU , Songshan JIANG , Guoyuan YUAN , Huidong QIU . Preparation, functional modification, and applications of Fe3O4 nanoparticles. Chinese Journal of Inorganic Chemistry, 2026, 42(7): 1383-1411. doi: 10.11862/CJIC.20250344

    18. [18]

      Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416

    19. [19]

      Wei LI , Jianjie XU , Linlin WANG , Chuanbing HOU , Hongliang HAN , Qionghua JIN . Synthesis, structure, and photocatalytic properties of {PMo12}-based rare-earth tetraisopropyl ethylenediphosphonate complexes. Chinese Journal of Inorganic Chemistry, 2026, 42(10): 2077-2091. doi: 10.11862/CJIC.20260220

    20. [20]

      Shengwen XU , Longlong YANG , Houji CAO , Deshuang TU , Xing WEI , Changsheng LU , Hong YAN . Research progress on light-induced functionalization of polyhedral carborane clusters. Chinese Journal of Inorganic Chemistry, 2025, 41(11): 2187-2200. doi: 10.11862/CJIC.20250192

Metrics
  • PDF Downloads(9)
  • Abstract views(2926)
  • HTML views(392)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return