Highly selective synthesis of hydrazones and indoles from olefins

Tetrahedron Letters

Volumn 45, Issue 4, 2004, Pages 869-873

  Ahmed, Moballigh ^a   Jackstell, Ralf ^a   Seayad, Abdul Majeed ^a   Klein, Holger ^a   Beller, Matthias ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AROMATIC COMPOUND; HYDRAZINE; HYDRAZONE DERIVATIVE; INDOLE; INDOLE DERIVATIVE; LIGAND; PHOSPHINE DERIVATIVE; RHODIUM DERIVATIVE; TOLUENE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; GAS; HYDROFORMYLATION; SYNTHESIS;

EID: 0346787839     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.11.044     Document Type: Article

References (32)

1. (a) Reviews: Müller T.E., Beller M. Chem. Rev. 98:1998;675-703
2. (b) Beller M., Breindl C., Eichberger M., Hartung C.G., Seayad J., Thiel O.R., Tillack A., Trauthwein H. Synlett. 2002;1579-1594
3. (c) Seayad J., Tillack A., Hartung C.G., Beller M. Adv. Synth. Catal. 344:2002;795-813
4. (d) Nobis M., Driessen-Hölscher B. Angew. Chem., Int. Ed. 40:2001;3983
5. (e) Brunet J.-J., Neibecker D. Togni A., Grützmacher H. Catalytic Heterofunctionalization. 2001;Wiley-VCH, Weinheim.
6. Eilbracht P., Bärfacker L., Buss C., Hollmann C., Kitsos-Rzychon B.E., Kranemann C.L., Rische T., Roggenbuck R., Schmidt A. Chem. Rev. 99:1999;3329-3365.
7. (a) Selected examples: Törös S., Gemes-Pesci I., Heil B., Maho S., Tubar Z. Chem. Commun. 1992;585-589
8. (b) Baig T., Kalck P. Chem. Commun. 1992;1373-1374
9. (c) Baig T., Molinier J., Kalck P. J. Organomet. Chem. 455:1993;219-224
10. (d) Brunet J.J., Neibecker D., Agbossou F., Srivastav R.S. J. Mol. Catal. 87:1994;223-230
11. (e) Breit B. Tetrahedron Lett. 39:1998;5163-5166
12. (f) Schaffrath H., Keim W. J. Mol. Catal. 140:1999;107-113.
13. (a) Rische T., Bärfacker L., Eilbracht P. Eur. J. Org. Chem. 3:1999;653-660
14. (b) Rische T., Kitsos-Rzychon B., Eilbracht P. Tetrahedron. 54:1998;2723-2742
15. (c) Kranemann C.L., Eilbracht P. Synthesis. 1:1998;71
16. (d) Rische T., Eilbracht P. Synthesis. 11:1997;1331-1337.
17. Zimmermann B., Herwig J., Beller M. Angew. Chem., Int. Ed. 38:1999;2372-2375.
18. Seayad A., Ahmed M., Klein H., Jackstell R., Gross T., Beller M. Science. 297:2002;1676-1678 Ahmed M., Seayad A.M., Jackstell R., Beller M. J. Am. Chem. Soc. 125:2003;10311-10318.
19. Seayad A., Ahmed M., Klein H., Jackstell R., Gross T., Beller M. Science. 297:2002;1676-1678 Ahmed M., Seayad A.M., Jackstell R., Beller M. J. Am. Chem. Soc. 125:2003;10311-10318.
20. (a) For reviews see: Robinson B. The Fischer Indole Synthesis. 1982;John Wiley & Sons, Chichester
21. (b) Hughes D.L. Org. Prep. Proced. Int. 25:1993;607-623.
22. Köhling P., Schmidt A.M., Eilbracht P. Org. Lett. 18:2003;3213-3216.
23. +]: 190.14700, found: 190.14510.
24. (a) Beller M., Krauter J.G.E. J. Mol. Catal. 143:1999;31-39
25. (b) Herrmann W.A., Schmid R., Kohlpaintner C.W., Priermeier T. Organometallics. 14:1995;1961-1968
26. (c) Bahrmann H.B., Bergrath K., Kleiner H.-J., Lapper P., Naumann C., Peters D., Regnat D. J. Organomet. Chem. 520:1996;97-100
27. (d) Rampf F.A., Spiegler M., Herrmann W.A. J. Organomet. Chem. 582:1999;204-210.
28. Klein H., Jackstell R., Wiese K.-D., Röttger D., Beller M. Angew. Chem., Int. Ed. 40:2001;3408-3411.
29. (a) For an excellent review see: Kamer P.C.J., van Leeuwen P.W.N., Reek J.N.H. Acc. Chem. Res. 34:2001;895-904
30. (b) Kranenburg M., van der Bugt Y.E.M., Kamer P.C.J., van Leeuwen P.W.N.M. Organometallics. 14:1995;3081-3083.
31. (a) Gribble G.W. J. Chem. Soc., Perkin Trans. 1. 2000;1045
32. (b) Verspui G., Elbertse G., Sheldon F.A., Hacking M.A.P.J., Sheldon R.A. Chem. Commun. 2000;1363-1364.