Rhenium-catalyzed didehydroxylation of vicinal diols to alkenes using a simple alcohol as a reducing agent

Journal of the American Chemical Society

Volumn 132, Issue 33, 2010, Pages 11408-11409

  Arceo, Elena ^a   Ellman, Jonathan A ^a   Bergman, Robert G ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON SUGARS; DERIVED MATERIALS; GOOD YIELD; LOW-VALENT; LOWER REACTION TEMPERATURE; NEW SYSTEM; RHENIUM CARBONYL COMPLEXES; SIMPLE ALCOHOLS; VICINAL DIOLS;

OLEFINS; OXYGEN; RHENIUM; SUGAR (SUCROSE); UNSATURATED COMPOUNDS;

RHENIUM COMPOUNDS;

ALCOHOL; ALKENE DERIVATIVE; CARBONYL DERIVATIVE; REDUCING AGENT; RHENIUM;

ARTICLE; BIOMASS; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; DEOXYGENATION; HYDROXYLATION; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; TEMPERATURE;

ALCOHOLS; ALKENES; CATALYSIS; HYDROXYLATION; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; RHENIUM; STEREOISOMERISM;

EID: 77955804248     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja103436v     Document Type: Article

References (22)

1. Huber, G. W., Iborra, S., and Corma, A. Chem. Rev. 2006, 106, 4044
2. Corma, A., Iborra, S., and Velty, A. Chem. Rev. 2007, 107, 2411
3. Arceo, E., Marsden, P., Bergman, R. G., and Ellman, J. A. Chem. Commun. 2009, 3357
4. Block, E. In Organic Reactions; Dauben, W. G., Ed.; John Wiley & Sons: New York, 1984; Vol. 30.
5. Jang, D. O. and Joo, Y. H. Synth. Commun. 1998, 28, 871
6. Cook, G. K. and Andrews, M. A. J. Am. Chem. Soc. 1996, 118, 9448
7. Ziegler, J. E., Zdilla, M. J., Evans, A. J., and Abu-Omar, M. M. Inorg. Chem. 2009, 48, 9998
8. Ghosh, P., Fagan, P. J., Marshall, W. J., Hauptman, E., and Bullock, R. M. Inorg. Chem. 2009, 48, 6490
9. Vkuturi, S., Chapman, G., Ahmad, I., and Nicholas, K. M. Inorg. Chem. 2010, 49, 4744
10. Schlaf, M., Ghosh, P., Fagan, P. J., Hauptman, E., and Bullock, R. M. Adv. Synth. Catal. 2009, 351, 789
11. Shibahara, F. and Krische, M. J. Chem. Lett. 2008, 37, 1102
12. Yen, P. W. and Chou, T. C. Appl. Catal., A 1999, 182, 217
13. Verhoef, M. J., Creyghton, E. J., Peters, J. A., and vanBekkum, H. Chem. Commun. 1997, 1989
14. Maytum, H. C., Francos, J., Whatrup, D. J., and Williams, J. M. J. Chem.-Asian J. 2010, 5, 538
15. 5-Nonanone, and consequently 5-nonanol by hydrogenation, is available from renewable resources by catalytic upgrading of bio-oils through ketonization: Gartner, C. A., Serrano-Ruiz, J. C., Braden, D. J., and Dumesic, J. A. ChemSusChem 2009, 2, 1121
16. Sharpless, K. B., Umbreit, M. A., Nieh, M. T., and Flood, T. C. J. Am. Chem. Soc. 1972, 94, 6538
17. Gable, K. P. and Phan, T. N. J. Am. Chem. Soc. 1994, 116, 833
18. Zhu, Z. L., AlAjlouni, A. M., and Espenson, J. H. Inorg. Chem. 1996, 35, 1408
19. Pearlstein, R. M. and Davison, A. Polyhedron 1988, 7, 1981
20. Brown, S. N. and Mayer, J. M. Inorg. Chem. 1992, 31, 4091
21. Gable, K. P. and Juliette, J. J. J. J. Am. Chem. Soc. 1995, 117, 955
22. Herrmann, W. A., Marz, D., Herdtweck, E., Schafer, A., Wagner, W., and Kneuper, H. J. Angew. Chem., Int. Ed. Engl. 1987, 26, 462