Hydrogenation of carbon dioxide to formate catalyzed by a copper/1,8-diazabicyclo[5.4.0]undec-7-ene system

Advanced Synthesis and Catalysis

Volumn 357, Issue 7, 2015, Pages 1369-1373

  Watari, Ryo ^a   Kayaki, Yoshihito ^b   Hirano, Shin Ichi ^a   Matsumoto, Norio ^a   Ikariya, Takao ^b  

^a CENTRAL RESEARCH INSTITUTE OF ELECTRIC POWER INDUSTRY   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

1,8 diazabicyclo 5.4.0 undec 7 ene (DBU); carbon dioxide; copper; formates; hydrogenation

Indexed keywords

EID: 84930006779     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201500043     Document Type: Article

References (49)

1. M. Mikkelsen, M. Jørgensen, F. C. Krebs, Energy Environ. Sci. 2010, 3, 43-81.
2. S. Enthaler, J. von Langermann, T. Schmidt, Energy Environ. Sci. 2010, 3, 1207-1217
3. M. Grasemann, G. Laurenczy, Energy Environ. Sci. 2012, 5, 8171-8181.
4. Y. Inoue, H. Izumida, Y. Sasaki, H. Hashimoto, Chem. Lett. 1976, 5, 863-864.
5. P. G. Jessop, T. Ikariya, R. Noyori, Chem. Rev. 1995, 95, 259-272
6. C. Federsel, R. Jackstell, M. Beller, Angew. Chem. 2010, 122, 6392-6395
7. Angew. Chem. Int. Ed. 2010, 49, 6254-6257
8. W. Wang, S. Wang, X. Ma, J. Gong, Chem. Soc. Rev. 2011, 40, 3703-3727.
9. R. Tanaka, M. Yamashita, K. Nozaki, J. Am. Chem. Soc. 2009, 131, 14168-14169.
10. R. M. Bullock, Science 2013, 342, 1054-1055.
11. C.-C. Tai, T. Chang, B. Roller, P. G. Jessop, Inorg. Chem. 2003, 42, 7340-7341.
12. C. Federsel, A. Boddien, R. Jackstell, R. Jennerjahn, P. J. Dyson, R. Scopelliti, G. Laurenczy, M. Beller, Angew. Chem. 2010, 122, 9971-9974
13. Angew. Chem. Int. Ed. 2010, 49, 9777-9780
14. R. Langer, Y. Diskin-Posner, G. Leitus, L. J. W. Shimon, Y. Ben-David, D. Milstein, Angew. Chem. 2011, 123, 10122-10126
15. Angew. Chem. Int. Ed. 2011, 50, 9948-9952
16. C. Ziebart, C. Federsel, P. Anbarasan, R. Jackstell, W. Baumann, A. Spannenberg, M. Beller, J. Am. Chem. Soc. 2012, 134, 20701-20704.
17. C. Federsel, C. Ziebart, R. Jackstell, W. Baumann, M. Beller, Chem. Eur. J. 2012, 18, 72-75
18. Y. M. Badiei, W.-H. Wang, J. F. Hull, D. J. Szalda, J. T. Muckerman, Y. Himeda, E. Fujita, Inorg. Chem. 2013, 52, 12576-12586
19. M. S. Jeletic, M. T. Mock, A. M. Appel, J. C. Linehan, J. Am. Chem. Soc. 2013, 135, 11533-11536.
20. W. S. Mahoney, J. M. Stryker, J. Am. Chem. Soc. 1989, 111, 8818-8823
21. J.-X. Chen, J. F. Daeuble, D. M. Brestensky, J. M. Stryker, Tetrahedron 2000, 56, 2153-2166
22. J.-X. Chen, J. F. Daeuble, J. M. Stryker, Tetrahedron 2000, 56, 2789-2798
23. H. Shimizu, D. Igarashi, W. Kuriyama, Y. Yusa, N. Sayo, T. Saito, Org. Lett. 2007, 9, 1655-1657
24. H. Shimizu, T. Nagano, N. Sayo, T. Saito, T. Ohshima, K. Mashima, Synlett 2009, 19, 3143-3146
25. K. Junge, B. Wandt, D. Addis, S. Zhou, S. Das, S. Fleischer, M. Beller, Chem. Eur. J. 2011, 17, 101-105
26. S. W. Krabbe, M. A. Hatcher, R. K. Bowman, M. B. Mitchell, M. S. McClure, J. S. Johnson, Org. Lett. 2013, 15, 4560-4563.
27. P. Haynes, L. H. Slaugh, J. F. Kohnle, Tetrahedron Lett. 1970, 11, 365-368.
28. As reported by Denise and Sneeden, the Cu-containing bimetallic complex Pd2Cu2Cl6(Ph2PCH2PPh2)3 acts as a catalyst for CO2 hydrogenation yielding HCO2C2H5, whereas the Cu complexes [(CuCl)2(Ph2PCH2PPh2)]2 and [Cu3Cl2(Ph2PCH2PPh2)3]Cl exhibited no catalytic activity:, B. Denise, R. P. A. Sneeden, J. Organomet. Chem. 1981, 221, 111-116.
29. K. M. K. Yu, C. M. Y. Yeung, S. C. Tsang, J. Am. Chem. Soc. 2007, 129, 6360-6361
30. J. Liu, C. Guo, Z. Zhang, T. Jiang, H. Liu, J. Song, H. Fan, B. Han, Chem. Commun. 2010, 46, 5770-5772.
31. Very recently, a marked effect of modified DBU on the Rh-catalyzed hydrogenation of CO2 was reported:, Y.-N. Li, L.-N. He, X.-D. Lang, X.-F. Liu, S. Zhang, RSC Adv. 2014, 4, 49995-50002.
32. L. Zhang, J. Cheng, Z. Hou, Chem. Commun. 2013, 49, 4782-4784.
33. R. Shintani, K. Nozaki, Organometallics 2013, 32, 2459-2462
34. Sumby's group reported that an MOF containing Cu(NHC)2 linkers catalyzes the hydroboration of CO2:, A. Burgun, R. S. Crees, M. L. Cole, C. J. Doonan, C. J. Sumby, Chem. Commun. 2014, 50, 11760-11763.
35. K. Motokura, D. Kashiwame, A. Miyaji, T. Baba, Org. Lett. 2012, 14, 2642-2645
36. K. Motokura, D. Kashiwame, N. Takahashi, A. Miyaji, T. Baba, Chem. Eur. J. 2013, 19, 10030-10037.
37. I. Kaljurand, T. Rodima, A. Pihl, V. Mäemets, I. Leito, I. A. Koppel, M. Mishima, J. Org. Chem. 2003, 68, 9988-9993.
38. F. Hutschka, A. Dedieu, M. Eichberger, R. Fornika, W. Leitner, J. Am. Chem. Soc. 1997, 119, 4432-4443.
39. C. Bianchini, C. A. Ghilardi, A. Meli, S. Midollini, A. Orlandini, J. Organomet. Chem. 1983, 248, C 13 -C 16
40. C. Bianchini, C. A. Ghilardi, A. Meli, S. Midollini, A. Orlandini, Inorg. Chem. 1985, 24, 924-931
41. C. M. Wyss, B. K. Tate, J. Bacsa, T. G. Gray, J. P. Sadighi, Angew. Chem. Int. Ed. 2013, 52, 12920-12923
42. K. Nakamae, B. Kure, T. Nakajima, Y. Ura, T. Tanase, Chem. Asian J. 2014, 9, 3106-3110.
43. He's group reported the polyethyleneimine (PEI)/RhCl33H2O/CyPPh2 system for the hydrogenation of CO2, and suggested that the system would function by way of PEI working as both a base and a labile ligand on Rh species:, Y.-N. Li, L.-N. He, A.-H. Liu, X.-D. Lang, Z.-Z. Yang, B. Yu, C.-R. Luan, Green Chem. 2013, 15, 2825-2829.
44. CCDC 1052526 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
45. G. Sekar, A. DattaGupta, V. K. Singh, Tetrahedron Lett. 1996, 37, 8435-8436
46. K. G. Thakur, G. Sekar, Synthesis 2009, 2785-2789
47. E. Feng, H. Huang, Y. Zhou, D. Ye, H. Jiang, H. Liu, J. Org. Chem. 2009, 74, 2846-2849
48. W. Wei, X.-Y. Hu, X.-W. Yan, Q. Zhang, M. Cheng, J.-X. Ji, Chem. Commun. 2012, 48, 305-307
49. F.-W. Li, Q.-L. Suo, H.-L. Hong, N. Zhu, Y.-Q. Wang, L.-M. Han, Tetrahedron Lett. 2014, 55, 3878-3880.