Citation: Wang Hui, Zheng Yi, Pan Zhentao, Fu Hongliang, Ling Fei, Zhong Weihui. Progress of Frustrated Lewis Pairs in Catalytic Hydrogenation[J]. Chinese Journal of Organic Chemistry, ;2017, 37(2): 301-313. doi: 10.6023/cjoc201607046 shu

Progress of Frustrated Lewis Pairs in Catalytic Hydrogenation

Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals, College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014

Corresponding author: Zhong Weihui, weihuizhong@zjut.edu.cn
Received Date: 30 July 2016
Revised Date: 19 September 2016

Fund Project: the National Natural Science Foundation of China 21276238the National Natural Science Foundation of China 21676253

Figures(26)

Frustrated Lewis pairs (FLPs) catalyzed hydrogenation reaction is one of the hotspots in the current hydrogenation field. This kind of reaction has the advantages of environment friendly, no metal residue, etc., and has a potential prospect for industrial application. According to the category of the substrate, a brief review of the recent progress in the field of the FLPs-catalyzed hydrogenation as well as the asymmetric hydrogenation is depicted.
- frustrated Lewis pairs,
- catalytic hydrogenation,
- asymmetric catalysis,
- progress
1. [1]
  Welch, G. C.; Juan, R. R. S.; Masuda, J. D.; Stephan, D. W. Science 2006, 314, 1124. doi: 10.1126/science.1134230
2. [2]
  Spies, P.; Erker, G.; Kehr, G.; Bergander, K.; Fröhlich, R.; Grimme, S.; Stephan, D.W. Chem. Commun. 2007, 5072.
3. [3]
  Sumerin, V.; Schulz, F.; Nieger, M.; Leskelä, M.; Repo, T.; Rieger, B. Angew. Chem. Int. Ed. 2008, 47, 6001. doi: 10.1002/anie.200800935
4. [4]
  Holschumacher, D.; Bannenberg, T.; Hrib, C. G.; Jones, P. G.; Tamm, M. Angew. Chem. Int. Ed. 2008, 47, 7428. doi: 10.1002/anie.v47:39
5. [5]
  Lu, Z.-P.; Cheng, Z.-H.; Chen, Z.-X.; Weng, L.-H.; Li, Z.-H.; Wang, H.-D. Angew. Chem., Int. Ed. 2011, 50, 12227. doi: 10.1002/anie.v50.51
6. [6]
  Zaher, H.; Ashley, A. E.; Irwin, M.; Thompson, A. L.; Gutmann, M. J.; Krämer, T.; O'Hare, D. Chem. Commun., 2013, 49, 9755. doi: 10.1039/c3cc45889j
7. [7]
  Caputo, C. B.; Zhu, K.-L.; Vukotic, V. N.; Loeb, S. J.; Stephan, D. W. Angew. Chem. Int. Ed. 2013, 52, 960. doi: 10.1002/anie.201207783
8. [8]
  Chernichenko, K.; Kótai, B.; Pápai, I.; Zhivonitko, V.; Nieger, M.; Leskelä, M.; Repo; T. Angew. Chem., Int. Ed. 2015, 54, 1749. doi: 10.1002/anie.201410141
9. [9]
  Samigullin, K.; Georg, I.; Bolte, M.; Lerner, H. W.; Wagner, M. Chem. Eur. J. 2016, 22, 3478. doi: 10.1002/chem.v22.10
10. [10]
  Zheng, J.-H.; Lin, Y.-J.; Wang, H.-D. Dalton Trans. 2016, 45, 6088. doi: 10.1039/C5DT03815D
11. [11]
  Mo, Z.-B.; Rit, A.; Campos, J.; Kolychev, E. L.; Aldridge, S. J. Am. Chem. Soc. 2016, 138, 3306. doi: 10.1021/jacs.6b01170
12. [12]
  Wang, P.-A.; Sun, X.-L.; Gao, P. Chin. J. Org. Chem. 2011, 31, 1369 (in Chinese).
13. [13]
  Xu, Y.-Y.; Li, Z.; Maxim B.; Nie, W.-L. Prog. Chem. 2012, 24, 1526 (in Chinese).
14. [14]
  Chase, P. A.; Welch, G. C.; Jurca, T.; Stephan, D. W. Angew. Chem., Int. Ed. 2007, 46, 8050. doi: 10.1002/(ISSN)1521-3773
15. [15]
  Chase, P. A.; Jurca, T.; Stephan, D. W. Chem. Commun. 2008, 1701.
16. [16]
  Mohr, J.; Oestreich, M. Angew. Chem., Int. Ed. 2014, 53, 13278. doi: 10.1002/anie.201407324
17. [17]
  Wei, S.-M.; Feng, X.-Q.; Du, H.-F. Org. Biomol. Chem. 2016, 14, 8026. doi: 10.1039/C6OB01556E
18. [18]
  Farrell, J. M.; Heiden, Z. M.; Stephan, D. W. Organometallics 2011, 30, 4497. doi: 10.1021/om2005832
19. [19]
  Chatterjee, I.; Oestreich, M. Angew. Chem., Int. Ed. 2015, 54, 1965. doi: 10.1002/anie.201409246
20. [20]
  Jiang, C.-F.; Blacque, O.; Berke, H. Chem. Commun. 2009, 5518.
21. [21]
  Scott, D. J.; Fuchter, M. J.; Ashley, A. E. Angew. Chem., Int. Ed. 2014, 53, 10218. doi: 10.1002/anie.201405531
22. [22]
  Spies, P.; Schwendemann, S.; Lange, S.; Kehr, G.; Fröhlich, R.; Erker, G. Angew. Chem., Int. Ed. 2008, 47, 7543. doi: 10.1002/anie.v47:39
23. [23]
  Wang, G.; Chen, C.; Du, T.-Y.; Zhong, W.-H. Adv. Synth. Catal. 2014, 356, 1747. doi: 10.1002/adsc.201301007
24. [24]
  (a) Sumerin, V.; Chernichenko, K.; Nieger, M.; Leskelä, M.; Rieger, B.; Repo, T. Adv. Synth. Catal. 2011, 353, 2093.
  (b) Chernichenko, K.; Nieger, M.; Leskelä, M.; Repo, T. Dalton Trans. 2012, 41, 9029.
  (c) Sumerin, V.; Schulz, F.; Atsumi, M.; Wang, C.; Nieger, M.; Leskelä, M.; Repo, T.; Pyykkö, P.; Rieger, B. J. Am. Chem. Soc. 2008, 130, 14117.
25. [25]
  Farrell, J. M.; Posaratnanathan, R. T.; Stephan, D. W. Chem. Sci. 2015, 6, 2010. doi: 10.1039/C4SC03675A
26. [26]
  Mummadi, S.; Unruh, D. K.; Zhao, J.-Y.; Li, S.-H.; Krempner, C. J. Am. Chem. Soc. 2016, 138, 3286. doi: 10.1021/jacs.5b13545
27. [27]
  Schwendemann, S.; Frölich, R.; Kehr, G.; Erker, G. Chem. Sci. 2011, 2, 1842. doi: 10.1039/c1sc00124h
28. [28]
  (a) Parks, D. J.; Spence, R. E. v. H.; Piers, W. E. Angew. Chem., Int. Ed. Engl. 1995, 34, 809.
  (b) Parks, D. J.; Piers, W. E.; Yap, G. P. A. Organometallics 1998, 17, 5492.
29. [29]
  Wang, H.-D.; Fröhlich, R.; Kehr, G.; Erker, G. Chem. Commun. 2008, 5966.
30. [30]
  Greb, L.; Oña-Burgos, P.; Schirmer, B.; Grimme, S.; Stephan, D. W.; Paradies, J. Angew. Chem., Int. Ed. 2012, 51, 10164. doi: 10.1002/anie.201204007
31. [31]
  Erõs, G.; Mehdi, H.; Pápai, I.; Rokob, T. A.; Király, P.; Tárkányi, G.; Soós, T. Angew. Chem., Int. Ed. 2010, 49, 6559. doi: 10.1002/anie.201001518
32. [32]
  Inés, B.; Palomas, D.; Holle, S.; Steinberg, S.; Nicasio, J. A.; Alcarazo, M. Angew. Chem., Int. Ed. 2012, 51, 12367. doi: 10.1002/anie.v51.49
33. [33]
  (a) Greb, L.; Daniliuc, C. G.; Bergander, K.; Paradies, J. Angew. Chem., Int. Ed. 2013, 52, 5876.
  (b) Paradies, J. Angew. Chem., Int. Ed. 2014, 53, 3552.
34. [34]
  Hounjet, L. J.; Bannwarth, C.; Garon, C. N.; Caputo, C. B.; Grimme, S.; Stephan, D. W. Angew. Chem., Int. Ed. 2013, 52, 7492. doi: 10.1002/anie.201303166
35. [35]
  Wang, X.-W.; Kehr, G.; Daniliuc, C. G.; Erker, G. J. Am. Chem. Soc. 2014, 136, 3293. doi: 10.1021/ja413060u
36. [36]
  Chernichenko, K.; Madarász, Á.; Pápai, I.; Nieger, M.; Leskelä, M.; Repo, T. Nat. Chem. 2013, 5, 718. doi: 10.1038/nchem.1693
37. [37]
  Szeto, K. C.; Sahyoun, W.; Merle, N.; Castelbou, J. L.; Popoff, N.; Lefebvre, F.; Raynaud, J.; Godard, C.; Claver, C.; Delevoye, L.; Gauvinc, R. M.; Taoufik, M. Catal. Sci. Technol. 2016, 6, 882. doi: 10.1039/C5CY01372K
38. [38]
  Reddy, J. S.; Xu, B.-H.; Mahdi, T.; Fröhlich, R.; Kehr, G.; Stephan, D. W.; Erker, G. Organometallics 2012, 31, 5638. doi: 10.1021/om3006068
39. [39]
  Greb, L.; Oña-Burgos, P.; Kubas, A.; Falk, F. C.; Breher, F.; Finkc, K.; Paradies, J. Dalton Trans. 2012, 41, 9056. doi: 10.1039/c2dt30374d
40. [40]
  Longobardi, L. E.; Tang, C.; Stephan, D. W. Dalton Trans. 2014, 43, 15723. doi: 10.1039/C4DT02648A
41. [41]
  Mahdi, T.; Stephan, D. W. J. Am. Chem. Soc. 2014, 136, 15809. doi: 10.1021/ja508829x
42. [42]
  Scott, D. J.; Fuchter, M. J.; Ashley, A. E. J. Am. Chem. Soc. 2014, 136, 15813. doi: 10.1021/ja5088979
43. [43]
  Mahdi, T.; Stephan, D. W. Angew. Chem., Int. Ed. 2015, 54, 8511. doi: 10.1002/anie.201503087
44. [44]
  Gyömöre, Á.; Bakos, M.; Földes, T.; Pápai, I.; Domján, A.; Soós, T. ACS Catal. 2015, 5, 5366. doi: 10.1021/acscatal.5b01299
45. [45]
  Geier, S. J.; Chase, P. A.; Stephan, D. W. Chem. Commun. 2010, 46, 4884. doi: 10.1039/c0cc00719f
46. [46]
  Erös, G.; Nagy, K.; Mehdi, H.; Pápai, I.; Nagy, P.; Király, P.; Tárkányi, G.; Soós, T. Chem. Eur. J. 2012, 18, 574. doi: 10.1002/chem.v18.2
47. [47]
  Chen, B.-L.; Wang, B.; Lin, G.-Q. J. Org. Chem. 2010, 75, 941. doi: 10.1021/jo902424m
48. [48]
  Segawa, Y.; Stephan, D. W. Chem. Commun. 2012, 48, 11963. doi: 10.1039/c2cc37190a
49. [49]
  Mahdi, T.; Heiden, Z. M.; Grimme, S.; Stephan, D. W. J. Am. Chem. Soc. 2012, 134, 4088. doi: 10.1021/ja300228a
50. [50]
  Longobardi, L. E.; Mahdi, T.; Stephan, D. W. Dalton Trans. 2015, 44, 7114. doi: 10.1039/C5DT00921A
51. [51]
  Mahdi, T.; Castillo, J. N. D.; Stephan, D. W. Organometallics 2013, 32, 1971. doi: 10.1021/om4000727
52. [52]
  Liu, Y.-B.; Du, H.-F. J. Am. Chem. Soc. 2013, 135, 12968. doi: 10.1021/ja406761j
53. [53]
  Liu Y. -B., Du H. -F. Acta Chim. Sinica 2014, 72, 771 (in Chinese) doi: 10.6023/A14040344
54. [54]
  Chen, D.-J.; Klankermayer, J. Chem. Commun. 2008, 2130.
55. [55]
  Chen, D.-J.; Wang, Y.-T.; Klankermayer, J. Angew. Chem., Int. Ed. 2010, 49, 9475. doi: 10.1002/anie.201004525
56. [56]
  Ghattas, G.; Chen, D.-J.; Pan, F.-F.; Klankermayer, J. Dalton Trans. 2012, 41, 9026. doi: 10.1039/c2dt30536d
57. [57]
  Chen, D.-J.; Leich, V.; Pan, F.-F.; Klankermayer, J. Chem. Eur. J. 2012, 18, 5184. doi: 10.1002/chem.v18.17
58. [58]
  Lindqvist, M.; Borre, K.; Axenov, K.; Kótai, B.; Nieger, M.; Leskelä, M.; Pápai, I.; Repo, T. J. Am. Chem. Soc. 2015, 137, 4038. doi: 10.1021/ja512658m
59. [59]
  (a) Mewald, M.; Oestreich, M. Chem. Eur. J. 2012, 18, 14079.
  (b) Hermeke, J.; Mewald, M.; Oestreich, M. J. Am. Chem. Soc. 2013, 135, 17537.
60. [60]
  Süsse, L.; Hermeke, J.; Oestreich, M. J. Am. Chem. Soc. 2016, 138, 6940. doi: 10.1021/jacs.6b03443
61. [61]
  Liu, Y.-B.; Du, H.-F. J. Am. Chem. Soc. 2013, 135, 6810. doi: 10.1021/ja4025808
62. [62]
  Wei, S.-M.; Du, H.-F. J. Am. Chem. Soc. 2014, 136, 12261. doi: 10.1021/ja507536n
63. [63]
  Ren, X.-Y.; Li, G.; Wei, S.-M.; Du, H.-F. Org. Lett. 2015, 17, 990. doi: 10.1021/acs.orglett.5b00085
64. [64]
  Ren, X.-Y.; Du, H.-F. J. Am. Chem. Soc. 2016, 138, 810. doi: 10.1021/jacs.5b13104
65. [65]
  Ashley, A. E.; Thompson, A. L.; O'Hare, D. Angew. Chem., Int. Ed. 2009, 48, 9839. doi: 10.1002/anie.v48:52
66. [66]
  Caputo, C. B.; Hounjet, L. J.; Dobrovetsky, R.; Stephan, D. W. Science 2013, 341, 1374. doi: 10.1126/science.1241764
67. [67]
  Hounjet, L. J.; Caputo, C. B.; Stephan, D. W. Dalton Trans. 2013, 42, 2629. doi: 10.1039/C2DT32711B
68. [68]
  Porwal, D.; Oestreich, M. Eur. J. Org. Chem. 2016, 3307.
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