Tandem amine and ruthenium-catalyzed hydrogenation of CO2to methanol

Journal of the American Chemical Society

Volumn 137, Issue 3, 2015, Pages 1028-1031

  Rezayee, Nomaan M ^a   Huff, Chelsea A ^a   Sanford, Melanie S ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON DIOXIDE; CATALYSIS; CATALYSTS; DIMETHYLFORMAMIDE; HYDROGENATION; METHANOL;

DIMETHYLAMINES; DIMETHYLAMMONIUM; DUAL ROLE; HOMOGENEOUS CATALYST; REACTION CONDITIONS; RUTHENIUM CATALYZED HYDROGENATION; RUTHENIUM COMPLEXES; TANDEM CATALYSIS;

RUTHENIUM COMPOUNDS;

AMINE; CARBAMIC ACID; CARBON DIOXIDE; FORMIC ACID; METHANOL; N,N DIMETHYLFORMAMIDE; RUTHENIUM COMPLEX;

ARTICLE; BATCH REACTOR; CATALYSIS; HYDROGENATION;

EID: 84921874741     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja511329m     Document Type: Article

References (66)

1. (a) Kamijo, T.; Sorimachi, Y.; Shimada, D.; Miyamoto, O.; Endo, T.; Nagayasu, H.; Mangiaracina, A. Energy Procedia 2013, 37, 813.
2. (b) Pera-Titus, M. Chem. Rev. 2013, 114, 1413.
3. (a) Figueroa, J. D.; Fout, T.; Plasynski, S.; McIlvried, H.; Srivastava, R. D. Int. J. Greenh. Gas Control 2008, 2, 9.
4. (b) Yang, H.; Xu, Z.; Fan, M.; Gupta, R.; Slimane, R. B.; Bland, A. E.; Wright, I. J. Environ. Sci. 2008, 20, 14.
5. (c) Macdowell, N.; Florin, N.; Buchard, A.; Hallett, J.; Galindo, A.; Jackson, G.; Adjiman, C. S.; Williams, C. K.; Shah, N.; Fennell, P. Energy Environ. Sci. 2010, 3, 1645.
6. (a) Corsten, M.; Ramírez, A.; Shen, L.; Koornneef, J.; Faaij, A. Int. J. Greenh. Gas Control 2013, 13, 59.
7. (b) Appel, A. M.; Bercaw, J. E.; Bocarsly, A. B.; Dobbek, H.; DuBois, D. L.; Dupuis, M.; Ferry, J. G.; Fujita, E.; Hille, R.; Kenis, P. J. A.; Kerfeld, C. A.; Morris, R. H.; Peden, C. H. F.; Portis, A. R.; Ragsdale, S. W.; Rauchfuss, T. B.; Reek, J. N. H.; Seefeldt, L. C.; Thauer, R. K.; Waldrop, G. L. Chem. Rev. 2013, 113, 6621.
8. (a) Darensbourg, D. J. Inorg. Chem. 2010, 49, 10765.
9. (b) Riduan, S. N.; Zhang, Y. G. Dalton Trans. 2010, 39, 3347.
10. (c) Dibenedetto, A.; Angelini, A.; Stufano, P. J. Chem. Technol. Biotechnol. 2014, 89, 334.
11. (a) Leitner, W. Angew. Chem., Int. Ed. 1995, 34, 2207.
12. (b) Grabow, L. C.; Mavrikakis, M. ACS Catal. 2011, 1, 365.
13. (c) Choudhury, J. ChemCatChem 2012, 4, 609.
14. (d) Li, Y. H.; Junge, K.; Beller, M. ChemCatChem 2013, 5, 1072.
15. (e) Li, Y. N.; Ma, R.; He, L. N.; Diao, Z. F. Catal. Sci. Technol. 2014, 4, 1498.
16. (a) Waller, D.; Stirling, D.; Stone, F. S.; Spencer, M. S. Faraday Discuss. Chem. Soc. 1989, 87, 107.
17. (b) Spencer, M. S. Top. Catal. 1999, 8, 259.
18. Martino, G.; Courty, P.; Marcilly, C.; Kochloefl, K.; Lunsford, J. H. Handbook of Heterogeneous Catalysis; Wiley-VCH: Weinheim, 1997; p 1801.
19. (a) Eisenschmid, T. C.; Eisenberg, R. Organometallics 1989, 8, 1822.
20. (b) Riduan, S. N.; Zhang, Y.; Ying, J. Y. Angew. Chem., Int. Ed. 2009, 48, 3322.
21. (c) Chakraborty, S.; Zhang, J.; Krause, J. A.; Guan, H. J. Am. Chem. Soc. 2010, 132, 8872.
22. (d) Huang, F.; Lu, G.; Zhao, L.; Li, H.; Wang, Z. X. J. Am. Chem. Soc. 2010, 132, 12388.
23. (e) Huang, F.; Zhang, C.; Jiang, J.; Wang, Z.-X.; Guan, H. Inorg. Chem. 2011, 50, 3816.
24. (f) Riduan, S. N.; Ying, J. Y.; Zhang, Y. G. ChemCatChem 2013, 5, 1490.
25. (g) Wang, B. J.; Cao, Z. X. R. Soc. Chem. Adv. 2013, 3, 14007.
26. (h) LeBlanc, F. A.; Piers, W. E.; Parvez, M. Angew. Chem., Int. Ed. 2014, 53, 789.
27. (i) Anker, M. D.; Arrowsmith, M.; Bellham, P.; Hill, M. S.; Kociok-Kohn, G.; Liptrot, D. J.; Mahon, M. F.; Weetman, C. Chem. Sci. 2014, 5, 2826.
28. (a) Ashley, A. E.; Thompson, A. L.; O'Hare, D. Angew. Chem., Int. Ed. 2009, 48, 9839.
29. (b) Ménard, G.; Stephan, D. W. J. Am. Chem. Soc. 2010, 132, 1796.
30. (c) Stephan, D. W.; Erker, G. Angew. Chem., Int. Ed. 2010, 49, 46.
31. (d) Sgro, M. J.; Stephan, D. W. Angew. Chem., Int. Ed. 2012, 51, 11343.
32. (e) Zhu, J.; An, K. Chem. - Asian J. 2013, 8, 3147.
33. (f) Courtemanche, M. A.; Legare, M. A.; Maron, L.; Fontaine, F. G. J. Am. Chem. Soc. 2013, 135, 9326.
34. (g) Courtemanche, M. A.; Legare, M. A.; Maron, L.; Fontaine, F. G. J. Am. Chem. Soc. 2014, 136, 10708.
35. (h) Wang, T.; Stephan, D. W. Chem. Commun. 2014, 50, 7007.
36. (i) Anker, M. D.; Arrowsmith, M.; Bellham, P.; Hill, M. S.; Kociok-Kohn, G.; Liptrot, D. J.; Mahon, M. F.; Weetman, C. Chem. Sci. 2014, 5, 2826.
37. (j) Fontaine, F. G.; Courtemanche, M. A.; Legare, M. A. Chem. - Eur. J. 2014, 20, 2990.
38. (a) Tominaga, K.; Sasaki, Y.; Kawai, M.; Watanabe, T.; Saito, M. J. Chem. Soc., Chem. Commun. 1993, 629.
39. (b) Tominaga, K.; Sasaki, Y.; Watanabe, T.; Saito, M. Bull. Chem. Soc. Jpn. 1995, 68, 2837.
40. Huff, C. A.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133, 18122.
41. Balaraman, E.; Gunanathan, C.; Zhang, J.; Shimon, L. J. W.; Milstein, D. Nat. Chem. 2011, 3, 609.
42. (a) Wesselbaum, S.; vom Stein, T.; Klankermeyer, J.; Leitner, W. Angew. Chem., Int. Ed. 2012, 51, 7499.
43. (b) Wesselbaum, S.; Moha, V.; Meuresch, M.; Brosinski, S.; Thenert, K. M.; Kothe, J.; Stein, T. v.; Englert, U.; Hölscher, M.; Klankermayer, J.; Leitner, W. Chem. Sci. 2015, 6, 693.
44. Yadav, M.; Linehan, J. C.; Karkamkar, A. J.; van der Eide, E.; Heldebrant, D. J. Inorg. Chem. 2014, 53, 9849.
45. (a) Jacquet, O.; Frogneux, X.; Das Neves Gomes, C.; Cantat, T. Chem. Sci. 2013, 4, 2127.
46. (b) Beydoun, K.; Vom Stein, T.; Klankermayer, J.; Leitner, W. Angew. Chem., Int. Ed. 2013, 52, 9554.
47. (c) Li, Y.; Sorribes, I.; Yan, T.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2013, 52, 12156.
48. (d) Beydoun, K.; Ghattas, G.; Thenert, K.; Klankermayer, J.; Leitner, W. Angew. Chem., Int. Ed. 2014, 53, 11010.
49. (e) Sorribes, I.; Junge, K.; Beller, M. Chem. - Eur. J. 2014, 20, 7878.
50. John, J. M.; Bergens, S. H. Angew. Chem., Int. Ed. 2011, 50, 10377.
51. Kuriyama, W.; Matsumoto, T.; Ogata, O.; Ino, Y.; Aoki, K.; Tanaka, S.; Ishida, K.; Kobayashi, T.; Sayo, N.; Saito, T. Org. Process Res. Dev. 2012, 16, 166.
52. (a) Balaraman, E.; Gnanaprakasam, B.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 2010, 132, 16756.
53. (b) Oldenhuis, N. J.; Dong, V. M.; Guan, Z. Tetrahedron 2014, 70, 4213.
54. TONs determined by GC-FID were in agreement with the values established by NMR. For example, for Table 3, entry 1, the TONs for methanol were 220 ± 31 (NMR) and 180 ± 23 (GC-FID). See Supporting Information (SI) for details.
55. (a) Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40.
56. (b) Hamilton, R. J.; Bergens, S. H. J. Am. Chem. Soc. 2006, 128, 13700.
57. (c) Clarke, M. L.; Diaz-Valenzuela, M. B.; Slawin, A. M. Z. Organometallics 2007, 26, 16.
58. (d) Saudan, L. A.; Saudan, C. M.; Debieux, C.; Wyss, P. Angew. Chem., Int. Ed. 2007, 46, 7473.
59. (e) Huff, C. A.; Sanford, M. S. ACS Catal. 2013, 3, 2412.
60. (f) Dub, P. A.; Henson, N. J.; Martin, R. L.; Gordon, J. C. J. Am. Chem. Soc. 2014, 136, 3505.
61. (a) Jessop, P. G.; Hsiao, Y.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1994, 116, 8851.
62. (b) Jessop, P. G.; Hsiao, Y.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 344.
63. (c) Jessop, P. G. The Handbook of Homogeneous Hydrogenation; Wiley-VCH: Weinheim, 2008; p 489.
64. 3OH (versus 99 turnovers for DMF hydrogenation). See SI for details.
65. 2 to DMF (see Table S3 for details).
66. 13C NMR spectroscopic analysis. See SI for details.