Guerbet reaction of primary alcohols leading to β-alkylated dimer alcohols catalyzed by iridium complexes

Journal of Organic Chemistry

Volumn 71, Issue 21, 2006, Pages 8306-8308

  Matsu Ura, Toyomi ^a   Sakaguchi, Satoshi ^a   Obora, Yasushi ^a   Ishii, Yasutaka ^a  

^a KANSAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

Β-ALKYLATED DIMER ALCOHOLS; ALDOL CONDENSATION; GUERBET REACTION;

ALDEHYDES; ALKYLATION; COMPLEXATION; DIMERS; HYDROGENATION; IRIDIUM;

ALCOHOLS;

ALCOHOL DERIVATIVE; ALKYL GROUP; DIMER; IRIDIUM COMPLEX;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; GUERBET REACTION; PROTON TRANSPORT; QUANTUM YIELD; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY;

EID: 33750018571     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061400t     Document Type: Article

References (15)

1. Guerbet, M. C. R. Acad. Sci. 1909, 49, 129.
2. Falbe, J.; Bahrmann, H.; Lipps, W.; Mayer, D. Alcohols, Aliphatic In Ullmann's Encyclopedia of Industrial Chemistry, 7th ed.; release 2006 on the web.
3. Gregorio, G.; Pregaglia, G. F.; Ugo, R. J. Organomet. Chem. 1972, 37, 385.
4. Burk, P. L.; Pruett, R. L.; Campo, K. S. J. Mol. Catal. 1985, 33, 1.
5. Burk, P. L.; Pruett, R. L.; Campo, K. S. J. Mol. Catal. 1985, 33, 15.
6. Carlini, C.; Macinai, A.; Raspolli Galletti, A. M.; Sbrana, G. J. Mol. Catal. A: Chem. 2004, 212, 65.
7. Taguchi, K.; Nakagawa, H.; Hirabayashi, T.; Sakaguchi, S.; Ishii, Y. J. Am. Chem. Soc. 2004, 126, 72.
8. Quite recently, β-alkylation of secondary alcohols with primary alcohols is reported via the in situ generation of methyl ketones. Fujita, K.; Kitatsuji, S.; Yamaguchi, T.; Hanasaka, F.; Yamaguchi, R. Org. Lett. 2005, 7, 4017.
9. (a) Cho, C. S.; Kim, B. T.; Kim, T.-J.; Shim, S. C. Tetrahedron Lett. 2002, 43, 7987.
10. (b) Cho, C. S.; Kim, B. T.; Kim, T.-J.; Shim, S. C. J. Org. Chem. 2001, 66, 9020.
11. (c) Cho, C. S.; Kim, B. T.; Kim, H.-S.; Kim, T.-J.; Shim, S. C. Organometaltics 2003, 22, 3608.
12. (a) Viladot Petit, J.-L.; De Moragas, M. EP 1358930, 2003. [CAN 139: 369354].
13. (b) Technical Service Report, Organische Produkte CPI; Henkel: Düsseldorf, 1980; p 28.
14. Tang, Z.; Zhou, Y.; Feng, Y. Appl. Catal., A: Gen. 2004, 273, 171.
15. Knifton, J. F.; Lin, J. J. J. Mol. Catal. 1993, 81, 27.