A Highly Active and Easily Accessible Cobalt Catalyst for Selective Hydrogenation of C=O Bonds

Journal of the American Chemical Society

Volumn 137, Issue 25, 2015, Pages 7998-8001

  Rösler, Sina ^a   Obenauf, Johannes ^a   Kempe, Rhett ^a  

^a UNIVERSITY OF BAYREUTH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; COBALT; HYDROGENATION; IRIDIUM; KETONES; PALLADIUM; RUTHENIUM;

CATALYST ACTIVATION; CATALYST LOADINGS; CO CATALYSTS; COBALT CATALYST; HYDROGENATION RATE; HYDROXYL GROUPS; PRECATALYSTS; SELECTIVE HYDROGENATION;

CATALYST SELECTIVITY;

ALDEHYDE DERIVATIVE; CARBONYL DERIVATIVE; COBALT; KETONE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CRYSTAL STRUCTURE; DEHYDROGENATION; ENANTIOSELECTIVITY; HYDROGEN BOND; HYDROGENATION; OXIDATION; PROTON TRANSPORT;

EID: 84934783336     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b04349     Document Type: Article

References (55)

1. The Handbook of Homogeneous Hydrogenation; de Vries, J. G., Elsevier, C. J., Eds.; Wiley-VCH Verlag GmbH: Weinheim, 2008.
2. Knijnenburg, Q.; Horton, A. D.; Heijden, H. v. d.; Kooistra, T. M.; Hetterscheid, D. G. H.; Smits, J. M. M.; Bruin, B. d.; Budzelaar, P. H. M.; Gal, A. W. J. Mol. Catal. A: Chem. 2005, 232, 151-159
3. Friedfeld, M. R.; Margulieux, G. W.; Schaefer, B. A.; Chirik, P. J. J. Am. Chem. Soc. 2014, 136, 13178-13181
4. Yu, R. P.; Darmon, J. M.; Milsmann, C.; Margulieux, G. W.; Stieber, S. C. E.; DeBeer, S.; Chirik, P. J. J. Am. Chem. Soc. 2013, 135, 13168-13184
5. Monfette, S.; Turner, Z. R.; Semproni, S. P.; Chirik, P. J. J. Am. Chem. Soc. 2012, 134, 4561-4564
6. Lin, T.-P.; Peters, J. C. J. Am. Chem. Soc. 2014, 136, 13672-13683
7. Gunderson, W. A.; Suess, D. L. M.; Fong, H.; Wang, X.; Hoffmann, C. M.; Cutsail, G. E., III; Peters, J. C.; Hoffman, B. M. J. Am. Chem. Soc. 2014, 136, 14998-15009
8. Srimani, D.; Mukherjee, A.; Gorldberg, A. F. G.; Leitus, G.; Diskin-Posner, Y.; Shimon, L. J. W.; Ben David, Y.; Milstein, D. Angew. Chem., Int. Ed. 2015, 10.1002/anie.201502418
9. Langer, R.; Leitus, G.; Ben-David, Y.; Milstein, D. Angew. Chem., Int. Ed. 2011, 50, 2120-2124
10. Langer, R.; Diskin-Posner, Y.; Leitus, G.; Shimon; Linda, J. W.; Ben-David, Y.; Milstein, D. Angew. Chem., Int. Ed. 2011, 50, 9948-9952
11. Ziebart, C.; Federsel, C.; Anbarasan, P.; Jackstell, R.; Baumann, W.; Spannenberg, A.; Beller, M. J. Am. Chem. Soc. 2012, 134, 20701-20704
12. Werkmeister, S.; Junge, K.; Wendt, B.; Alberico, E.; Jiao, H.; Baumann, W.; Junge, H.; Gallou, F.; Beller, M. Angew. Chem., Int. Ed. 2014, 53, 8722-8726
13. Zell, T.; Ben-David, Y.; Milstein, D. Angew. Chem., Int. Ed. 2014, 53, 4685-4689
14. Sonnenberg, J. F.; Lough, A. J.; Morris, R. H. Organometallics 2014, 33, 6452-6465
15. Gorgas, N.; Stöger, B.; Veiros, L. F.; Pittenauer, E.; Allmaier, G.; Kirchner, K. Organometallics 2014, 33, 6905-6914
16. Lagaditis, P. O.; Sues, P. E.; Sonnenberg, J. F.; Wan, K. Y.; Lough, A. J.; Morris, R. H. J. Am. Chem. Soc. 2014, 136, 1367-1380
17. Chakraborty, S.; Lagaditis, P. O.; Förster, M.; Bielinski, E. A.; Hazari, N.; Holthausen, M. C.; Jones, W. D.; Schneider, S. ACS Catal. 2014, 4, 3994-4003
18. Zell, T.; Ben-David, Y.; Milstein, D. Catal. Sci. Technol. 2015, 5, 822-826
19. Mazza, S.; Scopelliti, R.; Hu, X. Organometallics 2015, 34, 1538-1545
20. Zhang, G.; Vasudevan, K. V.; Scott, B. L.; Hanson, S. K. J. Am. Chem. Soc. 2013, 135, 8668-8681
21. Zhang, G.; Hanson, S. K. Chem. Commun. 2013, 49, 10151-10153
22. Zhang, G.; Scott, B. L.; Hanson, S. K. Angew. Chem., Int. Ed. 2012, 51, 12102-12106
23. Brookhart, M.; Grant, B.; Volpe, A. F. Organometallics 1992, 11, 3920-3922
24. Zhang, G.; Hanson, S. K. Org. Lett. 2013, 15, 650-653
25. Gaertner, D.; Welther, A.; Rad, B. R.; Wolf, R.; Wangelin, A. J. v. Angew. Chem., Int. Ed. 2014, 53, 3722-3726
26. Michlik, S.; Kempe, R. Nat. Chem. 2013, 5, 140-144
27. Michlik, S.; Kempe, R. Angew. Chem., Int. Ed. 2013, 52, 6326-6329
28. Hille, T.; Irrgang, T.; Kempe, R. Chem.-Eur. J. 2014, 20, 5569-5572
29. Ruch, S.; Irrgang, T.; Kempe, R. Chem.-Eur. J. 2014, 20, 13279-13285
30. Schirmer, W.; Flörke, U.; Haupt, H. J. Z. Anorg. Allg. Chem. 1987, 545, 83-97
31. Benito-Garagorri, D.; Puchberger, M.; Mereiter, K.; Kirchner, K. Angew. Chem., Int. Ed. 2008, 47, 9142-9145
32. Benito-Garagorri, D.; Kirchner, K. Acc. Chem. Res. 2008, 41, 201-213
33. Benito-Garagorri, D.; Wiedermann, J.; Pollak, M.; Mereiter, K.; Kirchner, K. Organometallics 2007, 26, 217-222
34. Benito-Garagorri, D.; Becker, E.; Wiedermann, J.; Lackner, W.; Pollak, M.; Mereiter, K.; Kisala, J.; Kirchner, K. Organometallics 2006, 25, 1900-1913
35. Li, H.; Zheng, B.; Huang, K.-W. Coord. Chem. Rev. 2015, 293-294, 116-138
36. Obligacion, J. V.; Semproni, S. P.; Chirik, P. J. J. Am. Chem. Soc. 2014, 136, 4133-4136
37. Shaffer, D. W.; Johnson, S. I.; Rheingold, A. L.; Ziller, J. W.; Goddard, W. A.; Nielsen, R. J.; Yang, J. Y. Inorg. Chem. 2014, 53, 13031-13041
38. Khaskin, E.; Diskin-Posner, Y.; Weiner, L.; Leitus, G.; Milstein, D. Chem. Commun. 2013, 49, 2771-2773
39. Scheuermann, M. L.; Semproni, S. P.; Pappas, I.; Chirik, P. J. Inorg. Chem. 2014, 53, 9463-9465
40. Semproni, S. P.; Hojilla Atienza, C. C.; Chirik, P. J. Chem. Sci. 2014, 5, 1956-1960
41. Semproni, S. P.; Milsmann, C.; Chirik, P. J. J. Am. Chem. Soc. 2014, 136, 9211-9224
42. Schaefer, B. A.; Margulieux, G. W.; Small, B. L.; Chirik, P. J. Organometallics 2015, 34, 1307-1320
43. Fryzuk, M. D.; Leznoff, D. B.; Thompson, R. C.; Rettig, S. J. J. Am. Chem. Soc. 1998, 120, 10126-10135
44. The ligand synthesis is similarly easy. For instance, 96% isolated yield starting from commercially available educts for the PN5P ligand of 3.
45. The spin-only value for a Co(II) complex in a pentacoordinated ligand environment in the low spin state is 1.7 μB.
46. Qu, S.; Dang, Y.; Song, Ch.; Wen, M.; Huang, K. W.; Wang, Z.-X. J. Am. Chem. Soc. 2014, 136, 4974-4991
47. Irrgang, T.; Friedrich, D.; Kempe, R. Angew. Chem., Int. Ed. 2011, 50, 2183-2186
48. Haack, K.-J.; Hashiguchi, S.; Fujii, A.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. 1997, 36, 285-288
49. Noyori, R. Angew. Chem., Int. Ed. 2002, 41, 2008-2022
50. Clapham, S. E.; Hadzovic, A.; Morris, R. H. Coord. Chem. Rev. 2004, 248, 2201-2237
51. Sandoval, C. A.; Ohkuma, T.; Utsumi, N.; Tsutsumi, K.; Murata, K.; Noyori, R. Chem.-Asian J. 2006, 1, 102-110
52. Casey, C. P.; Beetner, S. E.; Johnson, J. B. J. Am. Chem. Soc. 2008, 130, 2285-2295
53. Casey, C. P.; Guan, H. J. Am. Chem. Soc. 2009, 131, 2499-2507
54. Morris, R. H. Chem. Soc. Rev. 2009, 38, 2282-2291
55. Morris, R. H. Acc. Chem. Res. 2015, 48, 1494-1502