Mechanism of the methyltrioxorhenium-catalyzed deoxydehydration of polyols: A new pathway revealed

Chemistry - A European Journal

Volumn 19, Issue 12, 2013, Pages 3827-3832

  Qu, Shuanglin ^a   Dang, Yanfeng ^a   Wen, Mingwei ^a   Wang, Zhi Xiang ^a  

^a UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

biomass; density functional calculations; deoxydehydration; hydrogen transfer; reaction mechanisms

Indexed keywords

DENSITY FUNCTIONALS; DEOXYDEHYDRATION; HYDROGEN TRANSFER; REACTION MECHANISM;

ALCOHOLS; BIOMASS; CATALYSIS; DENSITY FUNCTIONAL THEORY; HYDROGEN; POLYOLS;

RHENIUM COMPOUNDS;

ALCOHOL DERIVATIVE; ALKENE; METHYLTRIOXORHENIUM VII; ORGANOMETALLIC COMPOUND; POLYMER; POLYOL; REDUCING AGENT;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS; THERMODYNAMICS;

ALCOHOLS; ALKENES; CATALYSIS; MODELS, MOLECULAR; ORGANOMETALLIC COMPOUNDS; POLYMERS; REDUCING AGENTS; THERMODYNAMICS;

EID: 84874986340     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201204001     Document Type: Article

References (46)

1. P. Gallezot, Chem. Soc. Rev. 2012, 41, 1538-1558
2. X. Zhang, M. Tu, M. G. Paice, Bioeng. Res. 2011, 4, 246-257
3. J. C. Serrano-Ruiz, R. Luque, A. Sepulveda-Escribano, Chem. Soc. Rev. 2011, 40, 5266-5281
4. S. N. Naik, V. V. Goud, P. K. Rout, A. K. Dalai, Renewable Sustainable Energy Rev. 2010, 14, 578-597
5. A.-L. Marshall, P. J. Alaimo, Chem. Eur. J. 2010, 16, 4970-4980
6. G. W. Huber, A. Corma, Angew. Chem. 2007, 119, 7320-7338
7. Angew. Chem. Int. Ed. 2007, 46, 7184-7201
8. G. W. Huber, S. Iborra, A. Corma, Chem. Rev. 2006, 106, 4044-4098.
9. K. P. Gable, T. N. Phan, J. Am. Chem. Soc. 1994, 116, 833-839
10. G. K. Cook, M. A. Andrews, J. Am. Chem. Soc. 1996, 118, 9448-9449
11. K. P. Gable, J. J. Juliette, J. Am. Chem. Soc. 1996, 118, 2625-2633
12. K. P. Gable, F. A. Zhuravlev, J. Am. Chem. Soc. 2002, 124, 3970-3979
13. E. Arceo, P. Marsden, R. G. Bergman, J. A. Ellman, Chem. Commun. 2009, 3357-3359
14. J. E. Ziegler, M. J. Zdilla, A. J. Evans, M. M. Abu-Omar, Inorg. Chem. 2009, 48, 9998-10000
15. S. Vkuturi, G. Chapman, I. Ahmad, K. M. Nicholas, Inorg. Chem. 2010, 49, 4744-4746
16. I. Ahmad, G. Chapman, K. M. Nicholas, Organometallics 2011, 30, 2810-2818.
17. S. Bi, J. Wang, L. Liu, P. Li, Z. Lin, Organometallics 2012, 31, 6139-6147.
18. E. Arceo, J. A. Ellman, R. G. Bergman, J. Am. Chem. Soc. 2010, 132, 11408-11409.
19. M. Shiramizu, F. D. Toste, Angew. Chem. Int. Ed. 2012, 51, 8082-8086.
20. J. Yi, S. Liu, M. M. Abu-Omar, Chemsuschem 2012, 5, 1401-1404.
21. C. T. Lee, W. T. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789
22. B. Miehlich, A. Savin, H. Stoll, H. Preuss, Chem. Phys. Lett. 1989, 157, 200-206
23. A. D. Becke, J. Chem. Phys. 1993, 98, 5648
24. P. J. Stephens, F. J. Devlin, C. F. Chabalowski, M. J. Frisch, J. Phys. Chem. 1994, 98, 11623-11627.
25. Y. Zhao, D. G. Truhlar, Acc. Chem. Res. 2008, 41, 157-167
26. Y. Zhao, D. G. Truhlar, J. Chem. Theory Comput. 2009, 5, 324-333
27. P. Sliwa, J. Handzlik, Chem. Phys. Lett. 2010, 493, 273-278
28. A. D. Kulkarni, D. G. Truhlar, J. Chem. Theory Comput. 2011, 7, 2325-2332.
29. A. V. Marenich, C. J. Cramer, D. G. Truhlar, J. Phys. Chem. B 2009, 113, 6378-6396.
30. S.-Y. Tang, Q.-X. Guo, Y. Fu, Chem. Eur. J. 2011, 17, 13866-13876
31. R. Giri, Y. Lan, P. Liu, K. N. Houk, J.-Q. Yu, J. Am. Chem. Soc. 2012, 134, 14118-14126
32. M. B. Herbert, Y. Lan, B. K. Keitz, P. Liu, K. Endo, M. W. Day, K. N. Houk, R. H. Grubbs, J. Am. Chem. Soc. 2012, 134, 7861-7866
33. M. Lin, G.-Y. Kang, Y.-A. Guo, Z.-X. Yu, J. Am. Chem. Soc. 2012, 134, 398-405
34. P. Liu, X. Xu, X. Dong, B. K. Keitz, M. B. Herbert, R. H. Grubbs, K. N. Houk, J. Am. Chem. Soc. 2012, 134, 1464-1467
35. Y. Dang, Z.-X. Wang, X. Wang, Organometallics 2012, 31, 7222-7234
36. H.-S. Yeom, J. Koo, H.-S. Park, Y. Wang, Y. Liang, Z.-X. Yu, S. Shin, J. Am. Chem. Soc. 2012, 134, 208-211.
37. J. Hermans, L. Wang, J. Am. Chem. Soc. 1997, 119, 2707-2714
38. M. Strajbl, Y. Y. Sham, J. Villa, Z. T. Chu, A. Warshel, J. Phys. Chem. B 2000, 104, 4578-4584
39. Z. X. Yu, K. N. Houk, J. Am. Chem. Soc. 2003, 125, 13825-13830
40. Y. Chen, S. Ye, L. Jiao, Y. Liang, D. K. Sinha-Mahapatra, J. W. Herndon, Z.-X. Yu, J. Am. Chem. Soc. 2007, 129, 10773-10784
41. Y. Liang, S. Liu, Y. Xia, Y. Li, Z.-X. Yu, Chem. Eur. J. 2008, 14, 4361-4373
42. C.-G. Zhang, R. Zhang, Z.-X. Wang, Z. Zhou, S. B. Zhang, Z. Chen, Chem. Eur. J. 2009, 15, 5910-5919
43. H. Li, M. Wen, Z.-X. Wang, Inorg. Chem. 2012, 51, 5716-5727.
44. Gaussian 09, Revision A.02, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian, Inc. Wallingford CT, 2009.
45. K. A. Nolin, J. R. Krumper, M. D. Pluth, R. G. Bergman, F. D. Toste, J. Am. Chem. Soc. 2007, 129, 14684-14696
46. L. W. Chung, H. G. Lee, Z. Lin, Y.-D. Wu, J. Org. Chem. 2006, 71, 6000-6009.