H2-driven deoxygenation of epoxides and diols to alkenes catalyzed by methyltrioxorhenium

Inorganic Chemistry

Volumn 48, Issue 21, 2009, Pages 9998-10000

  Ziegler, Jeanette E ^a   Zdilla, Michael J ^b   Evans, Andrew J ^a   Abu Omar, Mahdi M ^a  

^a PURDUE UNIVERSITY   (United States)

^b Temple University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; EPOXIDE; HYDROGEN; METHYLTRIOXORHENIUM VII; ORGANOMETALLIC COMPOUND; OXYGEN;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

ALKENES; CATALYSIS; EPOXY COMPOUNDS; HYDROGEN; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXYGEN;

EID: 70350451288     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic901792b     Document Type: Article

References (31)

1. (a) Herrmann, W. A.; Kuhn, F. E. Acc. Chem. Res. 1997, 30, 169.
2. (b) Rudolph, J.; Reddy, K. L.; Chiang, J. P.; Sharpless, K. B. J. Am. Chem. Soc. 1997, 119, 6189.
3. (c) Jonsson, S. Y.; Färnegårdh, K.; Bäckvall, J.-E. J. Am. Chem. Soc. 2001, 123, 1365.
4. (d) Tullo, A. Chem. Eng. News 2004, 82, 15.
5. (a) Sharpless, K. B.; Umbreit, M. A.; Nieh, M. T.; Flood, T. C. J. Am. Chem. Soc. 1972, 94, 6538.
6. (b) Corey, E. J.; Hopkins, P. B. Tetrahedron Lett. 1982, 23, 1979.
7. Larock, R. C. Comprehensive Organic Transformations: A Guide to Functional Group Preparations; VCH: New York, 1993; pp 155-156.
8. (a) Gable, K. P. Organometallics 1994, 13, 2486.
9. (b) Zhu, Z.; Espenson, J. H. J. Mol. Catal. A 1995, 103, 87.
10. (c) Gable, K. P.; Brown, E. C. Organometallics 2000, 19, 944.
11. Cook, G. K.; Andrews, M. A. J. Am. Chem. Soc. 1996, 118, 9448.
12. (a) Huber, G. W.; Iborra, S.; Corma, A. Chem. Rev. 2006, 106, 4044.
13. (b) van Haveren, J.; Scott, E. L.; Sanders, J. Biofuels Bioprod. Biorefining Bioprod. 2008, 2, 41.
14. (c) See DOE report: Werpy, T., Petersen, G., Eds. Top Value Added Chemicals from Biomass, Vol. 1, 2004, http://wwwl.eere.energy. gov/biomass/pdfs/35523.pdf.
15. Arceo, E.; Marsden, P.; Bergman, R. G.; Ellman, J. A. Chem. Commun. 2009, 3357.
16. Ghosh, P.; Fagan, P. J.; Marshall, W. J.; Hauptman, E.; Bullock, R. M. Inorg. Chem. 2009, 48, 6490.
17. Kusserow, B.; Schimpf, S.; Claus, P. Adv. Synth. Catal. 2003, 345, 89.
18. Childers, K. G.; Dreher, S. D.; Lee, JÜ Williams, J. M. Org. Process Res. Dev. 2006, 10, 934.
19. Zhu, Z.; Al-Ajlouni, A. M.; Espenson, J. H. Inorg. Chem. 1996, 35, 1408.
20. (a) Gable, K. P.; AbuBaker, A.; Zeintara, K.; Wainwright, A. M. Organometalllics 1999, 18, 173.
21. (b) Gable, K. P.; Juliette, J. J. J. Am. Chem. Soc. 1995, 117, 955.
22. (a) Felixberger, J. K.; Kuchler, J. G.; Herdtweck, E.; Paciello, R. A.; Herrmann, W. A. Angew. Chem., Int. Ed. Engl. 1988, 27, 946.
23. (b) Abu-Omar, M. M.; Appelman, E. H.; Espenson, J. H. Inorg. Chem. 1996, 35, 7751.
24. 2 form MDO probably via a [3+2] mechanism. (a) Coliman, J. P.; Slaughter, L. M.; Eberspacher, T. S.; Strassner, T.; Brauman, J. I. Inorg. Chem. 2001, 40, 6272.
25. (b) Dehestani, A.; Lam, W. H.; Hrovat, D. A.; Davidson, E. R.; Borden, W. T.; Mayer, J.M. J. Am. Chem. Soc. 2005, 127, 3423.
26. (a) Herrmann, W. A.; Fischer, R. W.; Marz, D. W. Angew. Chem., Int. Ed. Engl. 1991, 30, 1638.
27. (b) Espenson, J. H. Chem. Commun. 1999, 479.
28. Owens, G. S.; Arias, J.; Abu-Omar, M. M. Catal. Today 2000, 55, 317.
29. (a) Nolin, K. A.; Krumper, J. R.; Pluth, M. D.; Bergman, R. G.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 1468.
30. (b) Du, G.; Fanwick, P. E.; Abu-Omar,M. M, J. Am. Chem. Soc. 2007, 129, 5180.
31. (c) Reis, P. M.; Costa, P. J.; Romao, C. C.; Fernandes, J. A.; Calhorda, M, J.; Royo, B. Dalton Trans. 2008, 1727.