Aromatic carbonyl compound reduction and pinacol coupling processes mediated by titanocene(III)/Zn in water

Synthesis

Volumn , Issue 15, 2005, Pages 2619-2622

  Oller López, Juan L ^a   Campaña, Araceli G ^a   Cuerva, Juan M ^a   Oltra, J Enrique ^a  

^a UNIVERSITY OF GRANADA   (Spain)

Author keywords

Green chemistry; Radical reactions; Titanium; Water; Zinc

Indexed keywords

ALDEHYDES; CATALYSTS; KETONES; REACTION KINETICS; REDUCTION; TITANIUM; WATER; ZINC;

ARYL KETONES; GREEN-CHEMISTRY; RADICAL REACTIONS; SEA WATER;

AROMATIC COMPOUNDS;

ACETOPHENONE; ALDEHYDE; AROMATIC COMPOUND; CARBONYL DERIVATIVE; COLLIDINE; FREE RADICAL; KETONE; SEA WATER; TITANOCENE; WATER; ZINC;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL STRUCTURE; HYDROLYSIS; PINACOL REARRANGEMENT; PROTON NUCLEAR MAGNETIC RESONANCE; RADICAL REACTION; REDUCTION; STEREOCHEMISTRY; STOICHIOMETRY;

EID: 26844446391     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-872163     Document Type: Article

References (31)

1. (a) Engberts, J. B. F. N.; Blandamer, M. J. Chem. Commun. 2001, 1701.
2. (b) Ribe, S.; Wipf, P. Chem. Commun. 2001, 299.
3. (c) Lindström, U. M. Chem. Rev. 2002, 102, 2751.
4. For excellent overviews on contemporary free-radical chemistry, see: (a) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1996.
5. (b) Radicals in Organic Synthesis, Vol. 1,2; Renaud, P.; Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001.
6. RajanBabu, T. V.; Nugent, W. A. J. Am. Chem. Soc. 1994, 116, 986.
7. Barrero, A. F.; Oltra, J. E.; Cuerva, J. M.; Rosales, A. J. Org. Chem. 2002, 67, 2566.
8. Enemærke, R. J.; Larsen, J.; Skrydstrup, T.; Daasbjerg, K. J. Am. Chem. Soc. 2004, 126, 7853.
9. (a) Gansäuer, A. Chem. Commun. 1997, 457.
10. (b) Gansäuer, A.; Bauer, D. J. Org. Chem. 1998, 63, 2070.
11. For exhaustive reviews on the chemistry of bis(cyclopentadienyl) titanium(III) chloride in organic solvents, see: (a) Gansäuer, A.; Bluhm, H. Chem. Rev. 2000, 100, 2771.
12. (b) Gansäuer, A.; Pierobon, M. In Radicals in Organic Synthesis, Vol. 2; Renaud, P.; Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001, 207-220.
13. (c) Gansäuer, A.; Rinker, B. Tetrahedron 2002, 58, 7017.
14. (d) Gansäuer, A.; Narayan, S. Adv. Synth. Catal. 2002, 344, 465.
15. (e) Gansäuer, A.; Rinker, B. In Titanium and Zirconium in Organic Synthesis; Marek, I., Ed.; Wiley-VCH: Weinheim, 2002, 435-450.
16. (f) Gansäuer, A.; Lauterbach, T.; Narayan, S. Angew. Chem. Int. Ed. 2003, 42, 5556.
17. Barden, M. C.; Schwartz, J. J. Am. Chem. Soc. 1996, 118, 5484.
18. Barrero, A. F.; Rosales, A.; Cuerva, J. M.; Gansäuer, A.; Oltra, J. E. Tetrahedron Lett. 2003, 44, 1079.
19. Fürstner, A.; Csuk, R.; Rohrer, C.; Weidmann, H. J. Chem. Soc., Perkin Trans. 1 1988, 1729.
20. 2 solution in deoxygenated water became only yellow after ten hours stirring. When we added Zn, however, the color of the solution immediately changed to green and, after a couple of minutes, to blue.
21. (a) Sekutowski, D. G.; Stucky, G. D. Inorg. Chem. 1975, 14, 2192.
22. (b) Sekutowski, D.; Jungst, R.; Stucky, G. D. Inorg. Chem. 1978, 17, 1848.
23. (c) Stephan, D. W. Organometallics 1992, 11, 996.
24. Tsuzuki, S.; Honda, K.; Uchimaru, T.; Mikami, M.; Tanabe, K. J. Am. Chem. Soc. 2002, 124, 104.
25. Ganguly, B.; Fuchs, B. J. Org. Chem. 2000, 65, 558.
26. Enemærke, R. J.; Larsen, J.; Hjøllund, G. H.; Skrydstrup, T.; Daasbjerg, K. Organometallics 2005, 24, 1252.
27. 2 is not too expensive (10 g = 28.50, Aldrich catalogue), but Zn dust is considerably cheaper (1 Kg = 21.70).
28. Gansäuer, A.; Bluhm, H.; Pierobon, M. J. Am. Chem. Soc. 1998, 120, 12849.
29. Tanaka, K.; Kishigami, S.; Toda, F. J. Org. Chem. 1990, 55, 2981.
30. McDonough, W.; Braungart, M.; Anastas, P. T.; Zimmerman, J. B. Environ. Sci. Technol. 2003, 435A.
31. Mediterranean Sea water was taken from 'Las Acacias' beach, Malaga (Spain), in August 2004.