Triruthenium dodecacarbonyl/triphenylphosphine catalyzed dehydrogenation of primary and secondary alcohols

Tetrahedron

Volumn 60, Issue 5, 2004, Pages 1065-1072

  Meijer, R H ^a   Ligthart, G B W L ^a   Meuldijk, J ^a   Vekemans, J A J M ^a   Hulshof, L A ^a   Mills, A M ^b   Kooijman, H ^b   Spek, A L ^b  

^a EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

Alcohols; Catalytic dehydrogenation; Hydride acceptors; Ligands; Triruthenium dodecacarbonyl catalyst

Indexed keywords

ACETYLENE DERIVATIVE; ALCOHOL; ALDEHYDE; KETONE; PHOSPHINE DERIVATIVE; RUTHENIUM DERIVATIVE;

ARTICLE; CATALYSIS; DEHYDROGENATION; ELECTRON; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; OPPENAUER OXIDATION; PRIORITY JOURNAL; REDUCTION KINETICS; SYNTHESIS;

EID: 0346339649     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.11.082     Document Type: Article

References (27)

1. Sheldon R.A., van Santen R.A. Catalytic oxidations: principles and applications. 1995;World Scientific, Singapore. p 239.
2. Aranyos A., Csjernyik G., Szabo K., Bäckvall J.-E. Chem. Commun. 1999;351.
3. Wang G.-Z., Bäckvall J.-E. J. Chem. Soc., Chem. Commun. 1992;337.
4. Tomioka H., Takai K., Oshima K., Nozaki H. Tetrahedron Lett. 22:1981;1605.
5. Ito T., Horino H., Koshiro Y., Yamamoto A. Bull. Chem. Soc. Jpn. 55:1982;504.
6. Menashe N., Shvo Y. Organometallics. 10:1991;3885.
7. Tolman C.A. Chem. Rev. 77:1977;313.
8. Van Leeuwen P.W.N.M., Kamer P.C.J., Reek J.N.H. Pure Appl. Chem. 71:1999;1443.
9. Dierkes P., Van Leeuwen P.W.N.M. J. Chem. Soc., Dalton Trans. 1999;1519.
10. Van der Veen L.A., Keeven P.H., Schoenmaker G.C., Reek J.N.H., Kamer P.C.J., Van Leeuwen P.W.N.M., Lutz M., Spek A.L. Organometallics. 19:2000;872.
11. Van Leeuwen P.W.N.M., Kamer P.C.J., Reek J.N.H. CATTECH. 3:2000;164.
12. Chatt J., Shaw B.L., Field A.E. J. Chem. Soc. 1964;3466.
13. Beck C.M., Rathmill S.E., Jung Park Y., Chen J., Crabtree R.H. Organometallics. 18:1999;5311.
14. Shirakawa E., Yoshida H., Takaya H. Tetrahedron Lett. 38:1997;3759.
15. Naota T., Takaya H., Murahashi S.-I. Chem. Rev. 98:1998;2599.
16. Blum Y., Reshef D., Shvo Y. Tetrahedron Lett. 22:1981;1541.
17. Shvo Y., Blum Y., Reshef D., Maritmenzin M. J. Organomet. Chem. 226:1982;C21.
18. Almeida M.L.S., Kočovsky P., Bäckvall J.-E. J. Org. Chem. 61:1996;6587.
19. Shirakawa E., Yamasaki K., Hiyama T. Synthesis. 1998;271.
20. Mouriès V., Waschbüsch R., Carran J., Savignac P. Synthesis. 1998;1544.
21. Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; García-Granda, S.; Gould, R. O.; Smits, J. M. M.; Smykalla, C. The DIRDIF99 program system; Technical Report of the Crystallography Laboratory, University of Nijmegen: The Netherlands, 1999.
22. Sheldrick G.M. SHELXL97, Program for crystal structure refinement. 1997;University of Göttingen.
23. Wilson A.J.C. International tables for crystallography. Vol. C:1992;Kluwer Academic, Dordrecht.
24. Spek A.L. J. Appl. Crystallogr. 36:2003;7.
25. Yamazaki S., Taira Z. J. Organomet. Chem. 578:1999;61.
26. A significant solvent effect has been observed for these reactions. Apolar solvents such as p-xylene, decaline, polar solvents like NMP, DMA and DMSO and polar protic solvents like phenol and 3-ethyl-3-pentanol were studied. With phenol the best results were obtained (48% yield, 64% selectivity at 100 °C, 1 h).
27. Kiplinger J.L., King M.A., Fechtenkötter A., Arif A.M., Richmond T.G. Organometallics. 15:1996;5292.