Hydrogenation of esters catalyzed by ruthenium PN3-Pincer complexes containing an aminophosphine arm

Organometallics

Volumn 33, Issue 15, 2014, Pages 4152-4155

  Chen, Tao ^a,b   Li, Huaifeng ^a   Qu, Shuanglin ^c   Zheng, Bin ^a   He, Lipeng ^a   Lai, Zhiping ^a   Wang, Zhi Xiang ^c   Huang, Kuo Wei ^a  

^a KING ABDULLAH UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Saudi Arabia)

^b ZHEJIANG SCI TECH UNIVERSITY   (China)

^c INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ESTERIFICATION; ESTERS; HYDROGENATION; RUTHENIUM;

AIR-STABLE; AMINOPHOSPHINES; DFT STUDY; LOW TRANSITION; PINCER COMPLEXES; PRESENCE OF WATER; PROTON SHUTTLE; STABLE CATALYSTS;

RUTHENIUM COMPOUNDS;

EID: 84905836859     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om500549t     Document Type: Article

References (36)

1. Trost, B. M.; Fleming, I. Comprehensive organic synthesis: selectivity, strategy, and efficiency in modern organic chemistry, 1 st ed.; Pergamon Press: Oxford, England, 1991.
2. Seyden-Penne, J. Reductions by the alumino- and borohydrides in organic synthesis, 2 nd ed.; Wiley-VCH: New York, 1997.
3. Liu, K.; Song, C.; Subramani, V. Hydrogen and syngas production and purification technologies; Wiley and AIChE: Hoboken, NJ, 2010.
4. Kudo, A.; Miseki, Y. Chem. Soc. Rev. 2009, 38, 253-278
5. Esswein, A. J.; Nocera, D. G. Chem. Rev. 2007, 107, 4022-4047
6. Hayashi, J. I.; Hosokai, S.; Sonoyama, N. Process Saf. Environ. Prot. 2006, 84, 409-419
7. Levin, D. B.; Pitt, L.; Love, M. Int. J. Hydrogen Energy 2003, 29, 173-185
8. Dub, P. A.; Ikariya, T. ACS Catal. 2012, 2, 1718-1741
9. Otsuka, T.; Ishii, A.; Dub, P. A.; Ikariya, T. J. Am. Chem. Soc. 2013, 135, 9600-9603
10. Zhang, J.; Leitus, G.; Ben-David, Y.; Milstein, D. Angew. Chem., Int. Ed. 2006, 45, 1113-1115
11. Clarke, M. L.; Diaz-Valenzuela, M. B.; Slawin, A. M. Z. Organometallics 2007, 26, 16-19
12. Saudan, L. A.; Saudan, C.; Becieux, C.; Wyss, P. Angew. Chem., Int. Ed. 2007, 46, 7473-7476
13. Ito, M.; Ikariya, T. J. Synth. Org. Chem. Jpn. 2008, 66, 1042-1048
14. Takebayashi, S.; Bergens, S. H. Organometallics 2009, 28, 2349-2351
15. O, W. W. N.; Lough, A. J.; Morris, R. H. Chem. Commun. 2010, 46, 8240-8242
16. Kuriyama, W.; Ino, Y.; Ogata, O.; Sayo, N.; Saito, T. Adv. Synth. Catal. 2010, 352, 92-96
17. Ito, M.; Ootsuka, T.; Watari, R.; Shiibashi, A.; Himizu, A.; Ikariya, T. J. Am. Chem. Soc. 2011, 133, 4240-4242
18. Touge, T.; Hakamata, T.; Nara, H.; Kobayashi, T.; Sayo, N.; Saito, T.; Kayaki, Y.; Ikariya, T. J. Am. Chem. Soc. 2011, 133, 14960-14963
19. Balaraman, E.; Gunanathan, C.; Zhang, J.; Shimon, L. J. W.; Milstein, D. Nat. Chem. 2011, 3, 609-614
20. Zhang, J.; Balaraman, E.; Leitus, G.; Milstein, D. Organometallics 2011, 30, 5716-5724
21. Sun, Y.; Koehler, C.; Tan, R.; Annibale, V. T.; Song, D. Chem. Commun. 2011, 47, 8349-8351
22. Fogler, E.; Balaraman, E.; Ben-David, Y.; Leitus, G.; Shimon, L. J. W.; Milstein, D. Organometallics 2011, 30, 3826-3833
23. Han, Z.; Rong, L.; Wu, J.; Zhang, L.; Wang, Z.; Ding, K. Angew. Chem., Int. Ed. 2012, 51, 13041-13045
24. 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, 166-171
25. Spasyuk, D.; Smith, S.; Gusev, D. G. Angew. Chem., Int. Ed. 2012, 51, 2772-2775
26. Spasyuk, D.; Smith, S.; Gusev, D. G. Angew. Chem., Int. Ed. 2013, 52, 2538-2542
27. Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456-463
28. He, L.-P.; Chen, T.; Xue, D.-X.; Eddaoudi, M.; Huang, K.-W. J. Organomet. Chem. 2012, 700, 202-206
29. Chen, T.; He, L.-P.; Gong, D.; Yang, L.; Miao, X.; Eppinger, J.; Huang, K.-W. Tetrahedron Lett. 2012, 53, 4409-4412
30. He, L.-P.; Chen, T.; Gong, D.; Lai, Z.; Huang, K.-W. Organometallics 2012, 31, 5208-5211
31. Zeng, G.; Chen, T.; He, L.; Pinnau, I.; Lai, Z.; Huang, K.-W. Chem. Eur. J. 2012, 18, 15940-15943
32. Matsushita, H.; Ishiguro, S.; Ichinose, H.; Izumi, A.; Mizusaki, S. Chem. Lett. 1985, 731
33. Shi, L.; Liu, Y.; Liu, Q.; Wei, B.; Zhang, G. Green Chem. 2012, 14, 1372
34. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M. J.; Heyd, J.; Brothers, E. N.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A. P.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Gaussian, Inc., Wallingford, CT, 2009.
35. All structures were optimized in the gas phase at the M06/BSI level where BSI represents a basis set with 6-31G(d,p) for non-metal atoms and SDD for Ru. The energies were then improved by M06/BSII//M06/BSI single-point calculations with solvent effects accounted for by the SMD solvent model, using the experimental solvent (toluene). BSII denotes a basis set with 6-311++G(d,p) for non-metal atoms and SDD for Ru. All calculations were carried out using the Gaussian 09 program; more details are given in the Supporting Information.
36. Qu, S.; Dang, Y.; Song, C.; Wen, M.; Huang, K.-W.; Wang, Z.-X. J. Am. Chem. Soc. 2014, 136, 4974-4991