Nonmetal catalyzed hydrogenation of carbonyl compounds

Journal of the American Chemical Society

Volumn 136, Issue 45, 2014, Pages 15813-15816

  Scott, Daniel J ^a   Fuchter, Matthew J ^a   Ashley, Andrew E ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

KETONES;

1 ,4-DIOXANE; CARBONYL GROUPS; CATALYTIC HYDROGENATION; FRUSTRATED LEWIS PAIRS; LEWIS ACID; MILD REACTION CONDITIONS;

HYDROGENATION;

ALDEHYDE; BRONSTED BASE; CARBONYL DERIVATIVE; DIOXANE; KETONE; LEWIS ACID; NONMETAL; SOLVENT; 1,4-DIOXANE; DIOXANE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTROPHILICITY; HYDROGENATION; CHEMISTRY;

ALDEHYDES; CATALYSIS; DIOXANES; HYDROGENATION; KETONES; LEWIS ACIDS;

EID: 84910009573     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja5088979     Document Type: Article

References (29)

1. de Vries, J. G. and Elsevier, C. J. The Handbook of Homogeneous Hydrogenation; Wiley-VCH: Weinheim, Germany, 2008.
2. Darwish, M.; Wills, M. Catal. Sci. Technol. 2012, 2, 243
3. Welch, G. C.; Juan, R. R. S.; Masuda, J. D.; Stephan, D. W. Science 2006, 314, 1124
4. Chase, P. A.; Welch, G. C.; Jurca, T.; Stephan, D. W. Angew. Chem., Int. Ed. 2007, 46, 8050
5. Hounjet, L. J.; Stephan, D. W. Org. Process Res. Dev. 2014, 18, 385
6. Paradies, J. Synlett 2013, 24, 777
7. Wei, S.; Du, H. J. Am. Chem. Soc. 2014, 136, 12261-12264
8. Nyhlen, J.; Privalov, T. Dalton Trans. 2009, 29, 5780
9. Chase, P. A.; Jurca, T.; Stephan, D. W. Chem. Commun. 2008, 14, 1701
10. Chen, D.; Klankermayer, J. Chem. Commun. 2008, 18, 2130
11. Parks, D. J.; Piers, W. E. J. Am. Chem. Soc. 1996, 118, 9440
12. Parks, D. J.; Blackwell, J. M.; Piers, W. E. J. Org. Chem. 2000, 65, 3090
13. Piers, W. E.; Marwitz, A. J. V.; Mercier, L. G. Inorg. Chem. 2011, 50, 12252
14. Lindqvist, M.; Sarnela, N.; Sumerin, V.; Chernichenko, K.; Leskela, M.; Repo, T. Dalton Trans. 2012, 41, 4310
15. Longobardi, L. E.; Tang, C.; Stephan, D. W. Dalton Trans. 2014, 10.1039/C4DT02648A
16. Spies, P.; Erker, G.; Kehr, G.; Bergander, K.; Frohlich, R.; Grimme, S.; Stephan, D. W. Chem. Commun. 2007, 47, 5072
17. Ashley, A. E.; Thompson, A. L.; OHare, D. Angew. Chem., Int. Ed. 2009, 48, 9839
18. Sumerin, V.; Schulz, F.; Nieger, M.; Leskelä, M.; Repo, T.; Rieger, B. Angew. Chem., Int. Ed. 2008, 47, 6001
19. Stephan, D. W.; Greenberg, S.; Graham, T. W.; Chase, P.; Hastie, J. J.; Geier, S. J.; Farrell, J. M.; Brown, C. C.; Heiden, Z. M.; Welch, G. C.; Ullrich, M. Inorg. Chem. 2011, 50, 12338
20. Li, H.; Zhao, L.; Lu, G.; Huang, F.; Wang, Z. X. Dalton Trans. 2010, 39, 5519
21. Zhao, L.; Lu, G.; Huang, F.; Wang, Z. X. Dalton Trans. 2012, 41, 4674
22. Bergquist, C.; Bridgewater, B. M.; Harlan, C. J.; Norton, J. R.; Friesner, R. A.; Parkin, G. J. Am. Chem. Soc. 2000, 122, 10581
23. Arnett, E.; Wu, C. Y. J. Am. Chem. Soc. 1960, 82, 4999
24. Scott, D. J.; Fuchter, M. J.; Ashley, A. E. Angew. Chem., Int. Ed. 2014, 53, 10218-10222
25. Walling, C.; Bollyky, L. J. Am. Chem. Soc. 1964, 86, 3750
26. Berkessel, A.; Schubert, T. J. S.; Müller, T. N. J. Am. Chem. Soc. 2002, 124, 8693
27. Ashley, A. E.; Herrington, T. J.; Wildgoose, G. G.; Zaher, H.; Thompson, A. L.; Rees, N. H.; Kraemer, T.; OHare, D. J. Am. Chem. Soc. 2011, 133, 14727
28. Campbell, H. J.; Edward, J. T. Can. J. Chem. 1960, 38, 2109
29. Palm, V. A.; Haldna, U. L.; Talvik, A. J.; Patai, S. Basicity of carbonyl compounds; The Carbonyl Group: Vol. 1; John Wiley & Sons, Ltd.: Chichester, U.K., 1966, and references therein.