Ligand-promoted dehydrogenation of alcohols catalyzed by Cp*Ir complexes. A new catalytic system for oxidant-free oxidation of alcohols

Organic Letters

Volumn 9, Issue 1, 2007, Pages 109-111

  Fujita, Ken Ichi ^a   Tanino, Nobuhide ^a   Yamaguchi, Ryohei ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; IRIDIUM; LIGAND; ORGANOMETALLIC COMPOUND; OXIDIZING AGENT; WATER;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION;

ALCOHOLS; CATALYSIS; IRIDIUM; LIGANDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXIDANTS; OXIDATION-REDUCTION; WATER;

EID: 33846458263     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062806v     Document Type: Article

References (24)

1. (a) Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Brown, S. M.; Urch, C. J. Science 1996, 274, 2044.
2. (b) Sheldon, R. A.; Arenas, I. W. C. E.; ten Brink, G.-J.; Dijksman, A. Acc. Chem. Res. 2002, 35, 774.
3. (c) Csjernyik, G.; Éll, A. H.; Fadini, L.; Pugin, B.; Bäckvall, J.-E. J. Org. Chem. 2002, 67, 1657.
4. (d) Sigman, M. S.; Jensen, D. R. Acc. Chem. Res. 2006, 39, 221.
5. Noyori, R.; Aoki, M.; Sato, K. Chem. Commun. 2003, 1977.
6. (a) Almeida, M. L. S.; Beller, M.; Wang, G.-Z.; Bäckvall, J.-E. Chem. Eur. J. 1996, 2, 1533.
7. (b) Hanasaka, F.; Fujita, K.; Yamaguchi, R. Organometallics 2005, 24, 3422.
8. (a) Dobson, A.; Robinson, S. D. J. Organomet. Chem. 1975, 87, C52.
9. (b) Dobson, A.; Robinson, S. D. Inorg. Chem. 1977, 16, 137.
10. (c) Morton, D.; Cole-Hamilton, D. J. J. Chem. Soc., Chem. Commun. 1987, 248.
11. (d) Morton, D.; Cole-Hamilton, D. J. J. Chem. Soc., Chem. Commun. 1988, 1154.
12. (e) Morton, D.; Cole-Hamilton, D. J.; Utuk, I. D.; Paneque-Sosa, M.; Lopez-Poveda, M. J. Chem. Soc., Dalton Trans. 1989, 489.
13. (f) Ligthart, G. B. W. L.; Meijer, R. H.; Donners, M. P. J.; Meuldijk, J.; Vekemans, J. A. J. M.; Hulshof, L. A. Tetrahedron Lett. 2003, 44, 1507.
14. (g) Zhang, J.; Gandelman, M.; Shimon, L. J. W.; Rozenberg, H.; Milstein, D. Organometallics 2004, 23, 4026.
15. (h) Junge, H.; Beller, M. Tetrahedron Lett. 2005, 46, 1031.
16. (i) Adair, G. R. A.; Williams, J. M. J. Tetrahedron Lett. 2005, 46, 8233.
17. (j) van Buijtenen, J.; Meuldijk, J.; Vekemans, J. A. J. M.; Hulshof, L. A.; Kooijman, H.; Spek, A. L. Organometallics 2006, 25, 873.
18. Heterogeneous catalytic systems for the oxidant-free oxidation of alcohols have been also reported. (a) Choi, J. H.; Kim, N.; Shin, Y. J.; Park, J. Tetrahedron Lett. 2004, 45, 4607.
19. (b) Kim, W.-H.; Park, I. S.; Park, J. Org. Lett. 2006, 8, 2543.
20. Closely related dehydrogenative esterification of alcohols has been recently reported: (a) Zhao, J.; Hartwig, J. F. Organometallics 2005, 24, 2441.
21. (b) Zhang, J.; Leitus, G.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 2005, 127, 10840.
22. Evolution of dihydrogen was confirmed by the analysis of gas phase using a hydrogen sensor, although quantitative analysis was not carried out.
23. 1H} NMR analysis.
24. 2 was observed at δ 4.46 besides the signals of acetophenone (7%) and 1-phenylethanol (93%).