Direct oxidation of β-aryl substituted aldehydes to α,β-unsaturated aldehydes promoted by an o-anisidine-Pd(OAc) 2 Co-catalyst

Chemistry - An Asian Journal

Volumn 4, Issue 11, 2009, Pages 1712-1716

  Liu, Jie ^a   Zhu, Jin ^a   Jiang, Hualiang ^a,c   Wang, Wei ^a,b,c   Li, Jian ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b UNIVERSITY OF NEW MEXICO   (United States)

^c SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

Aldehydes; Anisidine; Organocatalysis; Palladium; Saegusa reaction

Indexed keywords

ANISIDINE; CATALYTIC SYSTEM; COCATALYST; DIRECT OXIDATION; ENOL SILYL ETHERS; GOOD YIELD; O-ANISIDINE; ORGANOCATALYSIS; UNSATURATED ALDEHYDES;

CATALYSIS; CATALYTIC OXIDATION; ETHERS; PALLADIUM; RATE CONSTANTS; REACTION KINETICS;

ALDEHYDES;

ALDEHYDE; ORGANOMETALLIC COMPOUND; PALLADIUM;

ARTICLE; CATALYSIS; CHEMISTRY; OXIDATION REDUCTION REACTION;

ALDEHYDES; CATALYSIS; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; PALLADIUM;

EID: 73649125827     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200900238     Document Type: Article

References (26)

1. P. Gallezot, D. Richard, Catal. Rev. 1998, 40, 81-126.
2. S. Burt, Int. J. Food Microbiol. 2004, 94, 223-253.
3. J. Cocchiara, C. S. Letizia, J. Lalko, A. Lapczynski, A. M. Api, Food Chem. Toxicol. 2005, 43, 867-923.
4. D. Almasi, D. A. Alonso, C. Najera, Tetrahedron: Asymmetry 2007, 18, 299-365.
5. S. B. Tsogoeva, Eur. J. Org. Chem. 2007, 1701-1716.
6. J. L. Vicario, D. Badía, L. Carrillo, Synthesis 2007, 2065-2092.
7. D. Enders, C. Grondal, M. R. M. Hüttl, Angew. Chem. 2007, 119, 1590-1601;
8. Angew. Chem. Int. Ed. 2007, 46, 1570-1581.
9. X.-H. Yu, W. Wang, Org. Biomol. Chem. 2008, 6, 2037-2046.
10. G. Tojo, M. Fernándes, in Oxidation of Alcohols to Aldehydes and Ketones: A Guide to Current Common Practice (Ed.: G. Tojo), Springer, Berlin, 2006, pp. 1.
11. D. J. Ager, Synthesis 1984, 384-398.
12. B. Breit, Acc. Chem. Res. 2003, 36, 264-275.
13. H. Neumann, A. Sergeev, M. Beller, Angew. Chem. 2008, 120, 4965-4969;
14. Angew. Chem. Int. Ed. 2008, 47, 4887-4891.
15. M. T. Crimmins, B. W. King, J. Am. Chem. Soc. 1998, 120, 9084-9085.
16. P. R. Mackie, C. E. Foster in Comprehensive Organic Group Transformations II, Vol. 3 (Eds.: A. R. Katritzky, R. J. K. Taylor, S. Jone), Elsevier, Dordrecht, 2004, pp. 59.
17. B. E. Maryanoff, A. B. Reitz, Chem. Rev. 1989, 89, 863-927.
18. R. C. Larock, Comprehensive Organic Transformations, Wiley, New York, 1999.
19. Y. Ito, T. Hirato, T. Saegusa, J. Org. Chem. 1978, 43, 1011-1013.
20. R. C. Larock, T. R. Higtower, G. A. Kraus, P. Hahn, D. Zhang, Tetrahedron Lett. 1995, 36, 2423-2426.
21. J. Zhu, J. Liu, R. Q. Ma, H. X. Xie, J. Li, H. L. Jiang, W. Wang, Adv. Synth. Catal. 2009, 351, 1229-1232.
22. K. E. Torraca, S. Kuwabe, S. L. Buchwald, J. Am. Chem. Soc. 2000, 122, 12907-12908.
23. G. Battistuzzi, S. Cacchi, G. Fabrizi, Org. Lett. 2003, 5, 777-780.
24. H. Schmidt, R. Behnisch, E. Schraufstatter, DE Patent 845, 195, 1950.
25. G. E. Stokker, W. F. Hoffman, A.W. Alberts, E. J. Cragoe Jr. , A. A. Deana, J. L. Gilfillan, J. W. Huff, F. C. Novello, J. D. Prugh, J. Med. Chem. 1985, 28, 347-358.
26. C.-H. Luo, Adv. Synth. Catal. 2007, 349, 1128-1140.