Frustrated Lewis Pairs: A new strategy for metal-free catalytic hydrogenation

Chinese Journal of Organic Chemistry

Volumn 31, Issue 9, 2011, Pages 1369-1376

  Wang, Pingan ^a   Sun, Xiaoli ^a   Gao, Peng ^a  

^a FOURTH MILITARY MEDICAL UNIVERSITY   (China)

Author keywords

Activation of molecular hydrogen; Frustrated lewis pairs; Metal free catalytic hydrogenation

Indexed keywords

EID: 83655203136     PISSN: 02532786     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (58)

1. Lewis, G N. Valence and the Structure of Atoms and Molecules, Chemical Catalogue Company, New York, 1923.
2. (a) Stephan, D. W; Erker, G Angew. Chem., Int. Ed 2010, 49, 46.
3. (b) Stephan, D. W In Catalysis without Precious Metals, Ed.: Bullock, R. M., Wiley-VCH Verlag GmbH & Co. KGa A, Weinheim, 2010, Chapter 11.
4. (c) Power, P. P. Nature 2010, 463, 171.
5. Brown, H. C.; Schlesinger, H. I.; Cardon, S. Z. J. Am. Chem. Soc. 1942, 64, 325.
6. Welch, G. C R.; Juan, R. S.; Masuda, J. D.; Stephan, D. W. Science 2006, 314, 1124.
7. (a) Rokob, T. A.; Hamza, A.; Stirling, A.; Pápai, I. J. Am. Chem. Soc. 2009, 131, 2029.
8. (b) Rokob, T. A.; Hamza, A.; Stirling, A.; Soós, T.; Pápai, I. Angew. Chem., Int. Ed. 2008, 47, 2435.
9. (c) Privalov, T. Dalton Trans. 2009, 1321.
10. (d) Privalov, T. Chem. Eur. J. 2009, 15, 1825.
11. (a) Guo, Y.; Li, S. Inorg. Chem. 2008, 47, 6212.
12. (b) Zhong, G; Chan, B.; Radom, L. J. Am. Chem. Soc. 2007, 129, 924.
13. Welch, G C.; Stephan, D. W J. Am. Chem. Soc. 2007, 129, 1880.
14. (a) Spies, P.; Erker, G; Kehr, G; Bergander, K.; Fröhlich, R.; Grimme, S.; Stephan, D. W. Chem. Commun. 2007, 5072.
15. (b) Spies, P.; Schwendemann, S.; Lange, S.; Kehr, G; Fröhlich, R.; Erker, G Angew. Chem., Int. Ed. 2008, 47, 7543.
16. Wang, H.; Fröhlich, R.; Kehr, G; Erker, G Chem. Commun. 2008, 5966.
17. Ullrich, M.; Lough, A. J.; Stephan, D. W. J. Am. Chem. Soc. 2009, 131, 52.
18. (a) Hermann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290.
19. (b) Moore, J. L.; Rovis, T. Top. Curr. Chem. 2009, 291, 77.
20. (c) Navarro, O.; Viciu, M. S. Annu. Rep. Prog. Chem., Sect. B: Org. Chem. 2010, 106, 243.
21. (a) Enders, D.; Niemeier, O.; Henseler, A. Chem. Rev. 2007, 107, 5606.
22. (b) Mercs, L.; Albrecht, M. Chem. Soc. Rev. 2010, 39, 1903.
23. Frey, G D.; Lavallo, V; Donnadieu, B. W.; Schoeller, W.; Bertrand, G Science 2007, 316, 439.
24. Holschumacher, D.; Bannenberg, T.; Hrib, C G.; Jones, P. G.; Tamm, M. Angew. Chem., Int. Ed. 2008, 47, 7428.
25. Chase, P. A.; Stephan, D. W. Angew. Chem., Int. Ed. 2008, 47, 7433.
26. Sumerin, V.; Schulz, F.; Nieger, M.; Leskelä, M.; Repo, T.; Rieger, B. Angew. Chem., Int. Ed. 2008, 47, 6001.
27. 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.
28. Jiang, C. F.; Blacque, O.; Berke, H. Chem. Commun. 2009, 5518.
29. Stephen, J. G; Stephan, D. W J. Am. Chem. Soc. 2009, 131, 3476.
30. Sakakura, T.; Choi, J. C.; Yasuda, H. Chem. Rev. 2007, 107, 2365.
31. Riduan, S.; Zhang, Y.; Ying, J. Angew. Chem., Int. Ed. 2009, 48, 3322.
32. Ashley, A.; Thompson, A.; O'Hare, D. Angew. Chem., Int. Ed. 2009, 48, 9839.
33. Berkefeld, A.; Piers, W. E.; Parvez, M. J. Am. Chem. Soc. 2010. 132, 10660.
34. Ménard, G; Stephan, D. W. J. Am. Chem. Soc. 2010, 132, 1796.
35. Erös, G; Mehdi, H.; Pápai, I.; Rokob, T. A.; Király, P.; Tárkányi, G; Soós, T. Angew. Chem., Int. Ed. 2010, 49, 6559.
36. Chase, P. A.; Jurca, T.; Stephan, D. W. Chem. Commun. 2008,1701.
37. Chen, D. J.; Klankermayer, J. Chem. Commun. 2008, 2130.
38. (a) Ouellet, S. G.; Walji, A. M.; Macmillan, D. W. C Acc. Chem. Res. 2007, 40, 1327.
39. (b) Melchiorre, P.; Marigo, M.; Carlone, A.; Bartoli, G. Angew. Chem., Int. Ed. 2008, 47, 6138.
40. (c) Li, G. L.; Antilla, J. C Org. Lett. 2009, 11, 1075.
41. (d) Thanh, B. N.; Bousserouel, H.; Wang, Q.; Guritte, F. Org. Lett. 2010, 12, 4705.
42. (e) Rueping, M.; Brinkmann, C.; Antonchick, A. P.; Atodiresei, I. Org. Lett. 2010, 12, 4604.
43. (a) Johnson, N. B.; Lennon, I. C.; Moran, P. H.; Ramsden, J. A. Ace. Chem. Res. 2007, 40, 1291.
44. (b) Zhang, W. C.; Chi, Y X.; Zhang, X. M. Ace. Chem. Res. 2007, 40, 1278.
45. Chen, D. J.; Wang, Y. T.; Klankermayer, J. Angew. Chem., Int. Ed. 2010, 49, 9475.
46. (a) Dureen, M. A.; Welch, G. C.; Gilbert, T. M.; Stephan, D. W. Inorg. Chem. 2009, 48, 9910.
47. (b) Inés, B.; Holle, S.; Goddard, R.; Alcarazo, M. Angew. Chem., Int. Ed. 2010, 49, 8389.
48. Welch, G. C.; Masuda, J. D.; Stephan, D. W. Inorg. Chem. 2006, 45, 478.
49. Mömming, C M.; Frömel, S.; Kehr, G.; Fröhlich, R.; Grimme, S.; Erker, G. J. Am. Chem. Soc. 2009, 131,12280.
50. Moebs-Sanchez, S.; Bouhadir, G.; Saffon, N.; Maron, L.; Bourissou, D. Chem. Commun. 2008, 3435.
51. McCahill, J. S. J.; Welch, G. C.; Stephan, D. W. Angew. Chem., Int. Ed. 2007, 46, 4968.
52. (a) Dureen, M. A.; Stephan, D. W. J. Am. Chem. Soc. 2009, 131, 8396.
53. (b) Zhao, X. X.; Gilbert, T. M.; Stephan, D. W. Chem. Eur. J. 2010, 16, 10304.
54. Mitu, S.; Baird, M. C. Can. J. Chem. 2006, 84, 225.
55. Stephan, D. W. Dalton Trans. 2009, 3129.
56. Otten, E.; Neu, R. C.; Stephan, D. W. J. Am. Chem. Soc. 2009, 131,9918.
57. (a) Tang, W. J.; Zhang, X. M. Chem. Rev. 2003, 103, 3029.
58. (b) Börner, A. Phosphorus Ligands in Asymmetrie Catalysis: Synthesis and Applications, Wiley-VCH, Verlag GmbH & Co. KGaA, Weinheim, 2008.