Facile and selective aerobic oxidation of arylalkanes to aryl ketones using cesium carbonate

Synthesis

Volumn , Issue 21, 2006, Pages 3617-3620

  Park, Kwanghee Koh ^a,b   Tsou, Lun K ^a   Hamilton, Andrew D ^a  

^a YALE UNIVERSITY   (United States)

^b Chungnam National University   (South Korea)

Author keywords

Aerobic oxidation; Aryl ketones; Arylalkanes; Cesium carbonate; Oxygenation

Indexed keywords

ALDEHYDES; CESIUM COMPOUNDS; KETONES; OXIDATION; REACTION KINETICS;

AEROBIC OXIDATION; ARYL KETONES; ARYLALKANES; CESIUM CARBONATE; OXYGENATION;

PARAFFINS;

ALDEHYDE; ALKANE DERIVATIVE; AMINO ACID; CARBONIC ACID; CESIUM CARBONATE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; OXYGENATION;

EID: 33751337075     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950189     Document Type: Article

References (22)

1. (a) Sen, A. Acc. Chem. Res. 1998, 31, 550.
2. (b) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
3. (a) Olah, G. A.; Molnár, A. Hydrocarbon Chemistry; Wiley: New York, 1995.
4. (b) The Activation of Dioxygen and Homogeneous Catalytic Oxidation; Barton, D. H. R.; Martell, A. E.; Sawyer, D. T., Eds.; Plenum: New York, 1993.
5. (c) Weissermel, K.; Arpe, H.-J. Industrial Organic Chemistry; VCH: New York, 1997.
6. Kawabata, H.; Hayashi, M. Tetrahedron Lett. 2004, 45, 5457; and references cited therein.
7. Kamata, K.; Kasai, J.; Yamaguchi, K.; Mizuno, N. Org. Lett. 2004, 6, 3577.
8. Ishii, Y.; Nakayama, K.; Takeno, M.; Sakaguchi, S.; Iwahama, T.; Nishiyama, Y. J. Org. Chem. 1995, 60, 3934.
9. Wang, J.-R.; Liu, L.; Wang, Y.-F.; Zhang, Y.; Deng, W.; Guo, Q.-X. Tetrahedron Lett. 2005, 46, 4647.
10. Yang, G.; Zhang, Q.; Miano, H.; Tong, X.; Xu, J. Org. Lett. 2005, 7, 263.
11. Nechab, M.; Einhorn, C.; Einhorn, J. Chem. Commun. 2004, 1500.
12. Khenkin, A. M.; Weiner, L.; Wang, Y.; Neumann, R. J. Am. Chem. Soc. 2001, 123, 8531.
13. Yamaguchi, K.; Mizuno, N. New J. Chem. 2002, 26, 972.
14. Lykakis, I. N.; Orfanopoulos, M. Tetrahedron Lett. 2004, 45, 7645.
15. Harvey, R. G.; Abu-shqara, E.; Yang, C. X. J. Org. Chem. 1992, 57, 6313.
16. Mori, H. JP 2002212126, 2002; Chem. Abstr. 2002, 137, 124994.
17. Perry, P. J.; Read, M. A.; Davies, R. T.; Gowan, S. M.; Reszka, A. P.; Wood, A. A.; Kelland, L. R.; Neidle, S. J. Med. Chem. 1999, 42, 2679.
18. Arafa, R. K.; Brun, R.; Wenzler, T.; Tanious, F. A.; Wilson, W. D.; Stephens, C. E.; Boykin, D. W. J. Med. Chem. 2005, 48, 5480.
19. Fieser, M.; Fieser, L. F. Reagents for Organic Synthesis, Vol. 7; Wiley: New York, 1979, 57.
20. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry. Part A; Kluwer: New York, 2000, 237-243.
21. Yamashina, K.; Namimatsu, K.; Chiba, N. JP 9,031,036, 1997; Chem. Abstr. 1997, 126, 231517.
22. Hauser, A.; Thurner, J.-U.; Hinzmann, B. J. Prakt. Chem. 1988, 330, 367.