Citation: Zhang Linli, Han Zhaobin, Zhang Lei, Li Mingxing, Ding Kuiling. Advances in Hydrogenation of Carboxylic Acid Derivatives and CO₂ Using Triphos as the Coordination Ligand[J]. Chinese Journal of Organic Chemistry, ;2016, 36(8): 1824-1838. doi: 10.6023/cjoc201603014 shu

Advances in Hydrogenation of Carboxylic Acid Derivatives and CO₂ Using Triphos as the Coordination Ligand

Zhang Linli ^a,b ,
Han Zhaobin ^b ,
Zhang Lei ^b ,
Li Mingxing ^a ,
Ding Kuiling ^a,b,*,,

a.
Department of Chemistry, College of Sciences, Shanghai University, Shanghai 200436
b.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Corresponding author: Ding Kuiling, kding@sioc.ac.cn
Received Date: 8 March 2016
Revised Date: 2 April 2016

Fund Project: Project supported by the National Natural Science Foundation of China Nos. 21472215, 21572254

Figures(26)

The reduction of carbon dioxide, carboxylic acids and their derivatives is one of the fundamental transformations both in academia and industry. Considering the increasing environmental issues, the use of molecular hydrogen as the reducing agent is especially attractive. Due to the mild reaction condition, high reactivity and easy modification of homogeneous catalysis, the development of highly efficient and selective homogeneous hydrogenation catalysts to achieve the goal is becoming a hot topic. Impressive progresses have been made using homogenous catalysts derived from transition metals and various ligands as catalysts. Among them, the catalytic system combined with a transition metal and CH₃C(CH₂PPh₂)₃ (triphos) usually shows unique reactivity and selectivity. This review will summarize the advance in the hydrogenation of carbon dioxide, carboxylic acids and their derivatives using Ru/triphos, Co/triphos and Cu/triphos as catalysts, as well as their reaction mechanisms.
- carboxylic acid and derivatives,
- carbon dioxide,
- triphos ligand,
- transition metal,
- hydrogenation,
- alcohol,
- amine
1. [1]
2. [2]
  Gribble, G. W. Chem. Soc. Rev. 1998, 27, 395.(b) Seyden-Penne, J. Reductions by the Alumino- and Borohydrides in Organic Synthesis, 2nd ed.; Wiley, New York, 1997.
3. [3]
  Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40.(b) Blaser, H.-U.; Federsel, H.-J. Asymmetric Catalysis on Industrial Scale, 2nd ed., Weinheim, Wiley-VCH, 2010.
4. [4]
  McAlees, A. J.; McCrindle, R. J. Chem. Soc. C 1969, 2425.
5. [5]
  Cokoja, M.; Bruckmeier, C.; Rieger, B.; Herrmann, W. A.; Kühn, F. E. Angew. Chem., Int. Ed. 2011, 50, 8510.(b) Zhang, L.; Han, Z.; Zhao, X.; Wang, Z.; Ding, K. Angew. Chem., Int. Ed. 2015, 54, 6186.
6. [6]
  Wang, W. H.; Himeda, H.; Muckerman, J. T.; Manbeck, G. F.; Fujita, F. Chem. Rev. 2015, 115, 12936.
7. [7]
  Nishimura, S. Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis, Wiley, New York, 2001.
8. [8]
  Rieke, R.; Thakur, D.; Roberts, B.; White, G. J. Am. Oil Chem. 1997, 74, 333.
9. [9]
  Stein, M.; Breit, B. Angew. Chem., Int. Ed. 2013, 52, 2231.
10. [10]
  de Vries, J. G.; Elsevier, C. J. The Handbook of Homogeneous Hydrogenation, Wiley, Weinheim, 2007.
11. [11]
  Grey, R. A.; Pez, G. P.; Wallo, A. J. Am. Chem. Soc. 1981, 103, 7536.
12. [12]
  Matteoli, U.; Menchi, G.; Bianchi, M.; Piacenti, F. J. Mol. Catal. 1988, 44, 347.
13. [13]
  Teunissen, H. T.; Elsevier, C. J. Chem. Commun. 1997, 667.
14. [14]
  Hewertson, W.; Watson, H. R. J. Chem. Soc. 1962, 1490.
15. [15]
  van Engelen, M. C.; Teunissen, H. T.; de Vries, J. G.; Elsevier, C. J. J. Mol. Catal. A: Chem. 2003, 206, 185.
16. [16]
  Bianchini, C.; Meli, A.; Peruzzini, M.; Vizza, F.; Zanobini, F. Coord. Chem. Rev. 1992, 120, 193.(b) Hierso, J.-C.; Amardeil, R.; Bentabet, E.; Broussier, R.; Gautheron, B.; Meunier, P.; Kalck, P. Coord. Chem. Rev. 2003, 236, 143.
17. [17]
  Bianchini, C.; Meli, A.; Peruzzini, M.; Vizza, F.; Frediani, P.; Ramirez, J. A. Organometallics 1990, 9, 226.
18. [18]
  Barbaro, P.; Bianchini, C.; Meli, A.; Moreno, M.; Vizza, F. Organometallics 2002, 21, 1430.
19. [19]
  Bianchini, C.; Meli, A.; Moneti, S.; Vizza, F. Organometallics 1998, 17, 2636.(b) Bianchini, C.; Masi, D.; Meli, A.; Peruzzini, M.; Vizza, F.; Zanobini, F. Organometallics 1998, 17, 2495.(c) Bianchini, C.; Meli, A.; Vizza, F. J. Organomet. Chem. 2004, 689, 4277.
20. [20]
  Barbaro, P.; Bianchini, C.; Frediani, P.; Meli, A.; Vizza, F. Inorg. Chem. 1992, 31, 1523.
21. [21]
  Mellone, I.; Bertini, F.; Gonsalvi, L.; Guerriero, A.; Peruzzini, M. Chimia 2015, 69, 331.
22. [22]
  Dub, P. A.; Ikariya, T. ACS Catal. 2012, 2, 1718.(b) Werkmeister, S.; Neumann, J.; Junge, K.; Beller, M. Chem. Eur. J. 2015, 21, 12226.
23. [23]
  Teunissen, H. T.; Elsevier, C. J. Chem. Commun. 1998, 1367.
24. [24]
  Berke, H. Book of Abstracts, XⅡth FECHEM Conference on Organometallic Chemistry, Prague, 1997, PL 9.
25. [25]
  Rosato, D. V.; Rosato, M. V. Plastic Product Material and Process Selection Handbook, Elsevier, North Holland, 2004.
26. [26]
  Furst, M. R. L.; Goff, R. L.; Quinzler, D.; Mecking, S.; Botting C. H.; Cole-Hamilon D. J. Green Chem. 2012, 12, 472.
27. [27]
  vom Stein, T.; Meuresch, M.; Limper, D.; Schmitz, M.; Hölscher; Coetzee, J.; Cole-Hamilton, D. J.; Klankermayer, J.; Leitner, W. J. Am. Chem. Soc. 2014, 136, 13217.
28. [28]
  Wesselbaum, S.; vom Stein, T.; Klankermayer, J.; Leitner, W. Angew. Chem., Int. Ed. 2012, 51, 7499.
29. [29]
  Boardman, B.; Hanton, M. J.; van Rensburg, H.; Tooze, R. P. Chem. Commun. 2006, 2289.
30. [30]
  Hanton, M. J.; Tin, S.; Boardman, B. J.; Miller, P. J. Mol. Catal. A: Chem. 2011, 346, 70.
31. [31]
  Li, Y. H.; Topf, C.; Cui, X. J.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2015, 54, 5196.
32. [32]
  Kilner, M.; Tyers, D. V.; Crabtree, S. P.; Wood, M. A. US 7709689, 2003 [Chem. Abstr. 2003, 139, 366612].
33. [33]
  Crabtree, S. P.; Tyers, D. V.; Sharif, M. WO 05/051907, 2005 [Chem. Abstr. 2005, 143, 43765].
34. [34]
  Rosi, L.; Frediani, M.; Frediani, P. J. Organomet. Chem. 2010, 695, 1314.
35. [35]
  Geilen, F. M. A.; Engendahl, B.; Harwardt, A.; Marquardt, W.; Klankermayer, J.; Leitner, W. Angew. Chem., Int. Ed. 2010, 49, 5510.
36. [36]
  Geilen, F. M. A.; Engendahl, B.; Hölscher, M.; Klankermayer, J.; Leitner, W. J. Am. Chem. Soc. 2011, 133, 14349.
37. [37]
  Phanopoulos, A.; White, A. J. P.; Long, N. J.; Miller, P. W. ACS Catal. 2015, 5, 2500.
38. [38]
  Cui, X. J.; Li, Y. H.; Topf, C.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2015, 54, 10596.
39. [39]
  Constable, D. J. C.; Dunn, P. J.; Hayler, J. D.; Humphrey, G. R.; Leazer, J. L.; Linderman, R. J.; Lorenz, K.; Manley, J.; Pearlman, B. A.; Wells, A.; Zaks, A.; Zhang, T. Y. Green Chem. 2007, 9, 411.
40. [40]
  Magro, A. A. N.; Eastham, G. R.; Cole-Hamilton, D. J. Chem. Commun. 2007, 3154.
41. [41]
  Dodds, D. L.; Coetzee, J.; Klankermayer, J.; Brosinski, S.; Leitner, W.; Cole-Hamilton, D. J. Chem. Commun. 2012, 48, 12249.
42. [42]
  Coetzee, J.; Dodds, D. L.; Klankermayer, J.; Brosinski, S.; Leitner, W.; Slawin, A. M. Z.; Col-Hamilton, D. J. Chem. Eur. J. 2013, 19, 11039.
43. [43]
  Cabrero-Antonino, J. R.; Alberico, E.; Junge, K.; Junge, H.; Beller M. Chem. Sci. 2016, 7, 3432.
44. [44]
  Meuresch, M.; Westhues, S.; Leitner, W.; Klankermayer, J. Angew. Chem., Int. Ed. 2016, 55, 1392.
45. [45]
  Cabrero-Antonino, J. R.; Sorribes, I.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2016, 55, 387.
46. [46]
  Huff, C. A.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 18122.(b) Li, Y. N.; He, L. N.; Liu, A. H.; Lang, X. D.; Yang, Z. Z.; Yu, B.; Luan, C. R. Green Chem. 2013, 15, 2825.(c) Khusnutdinova, J. R.; Garg, J. A.; Milstein, D. ACS Catal. 2015, 5, 2416.(d) Kothandaraman, J.; Goeppert, A.; Czaun, M.; Olah, G. A.; Prakash, G. K. S. J. Am. Chem. Soc. 2016, 138, 778.
47. [47]
  Wesselbaum, S.; Moha, V.; Meuresch, M.; Brosinski, S.; Thenert, K. M.; Kothe, J.; vom Stein, T.; Englert, U.; Holscher, M.; Klankermayer, J.; Leitner, W. Chem. Sci. 2015, 6, 693.
48. [48]
  Beydoun, K.; vom Stein, T.; Klankermayer, J.; Leitner, W. Angew. Chem., Int. Ed. 2013, 52, 9554.
49. [49]
  Li, Y.; Sorribes, I.; Yan, T.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2013, 52, 12156.
50. [50]
  Beydoun, K.; Ghattas, G.; Thenert, K.; Klankermayer, J.; Leitner, W. Angew. Chem., Int. Ed. 2014, 53, 11010.
51. [51]
  Beydoun, K.; Thenert, K.; Streng, E. S.; Brosinski, S.; Leitner, W.; Klankermayer, J. ChemCatChem 2016, 8, 135
52. [52]
  Li, Y.; Yan, T.; Junge, K.; Beller M. Angew. Chem., Int. Ed. 2014, 53, 10476.
53. [53]
  Savourey, S.; Lefevre, G.; Berthet, J.-C.; Cantat, T. Chem. Commun. 2014, 50, 14033.
54. [54]
  Sorribes, I.; Cabrero-Antonino, J. R.; Vicent, C.; Junge, K.; Beller, M. J. Am. Chem. Soc. 2015, 137, 13580.
55. [55]
  Korstanje, T. J.; van der Vlugt, J. I.; Elsevier, C. J.; de Bruin, B. Science 2015, 350, 298.
56. [56]
  Zall, C. M.; Linehan, J. C.; Appel A. M. ACS Catal. 2015, 5, 5301.
57. [57]
  Watari, R.; Kayaki, Y.; Hirano, S.; Matsumoto, N.; Ikariya, T. Adv. Synth. Catal. 2015, 357, 1369.
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Advances in Hydrogenation of Carboxylic Acid Derivatives and CO2 Using Triphos as the Coordination Ligand

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Advances in Hydrogenation of Carboxylic Acid Derivatives and CO₂ Using Triphos as the Coordination Ligand