Palladium-catalyzed oxidation of cyclohexanones to conjugated enones using molecular oxygen

Tetrahedron Letters

Volumn 48, Issue 39, 2007, Pages 6860-6862

  Tokunaga, Makoto ^a,b   Harada, Saki ^a,b   Iwasawa, Tetsuo ^a,b   Obora, Yasushi ^a,b   Tsuji, Yasushi ^a,b  

^a Graduate School of Science   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

5,5' DIMETHYL 2,2' BIPYRIDINE; BIPYRIDINE DERIVATIVE; CYCLOHEXANONE DERIVATIVE; OXYGEN; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; OXIDATION;

EID: 34548284970     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.07.181     Document Type: Article

References (30)

1. Punniyamurthy T., Velusamy S., and Iqbal J. Chem. Rev. 105 (2005) 2329-2363
2. Tokunaga M., Aoyama H., Shirogane Y., Obora Y., and Tsuji Y. Catal. Today 117 (2006) 138-140
3. Komano T., Iwasawa T., Tokunaga M., Obora Y., and Tsuji Y. Org. Lett. 7 (2005) 4677-4679
4. Tokunaga M., Shirogane Y., Aoyama H., Obora Y., and Tsuji Y. J. Organomet. Chem. 690 (2005) 5378-5382
5. Ebitani K., Motokura K., Mizugaki T., and Kaneda K. Angew. Chem., Int. Ed. 44 (2005) 3423-3426
6. Shimizu H., Onitsuka S., Egami H., and Katsuki T. J. Am. Chem. Soc. 127 (2005) 5396-5413
7. Iwasawa T., Tokunaga M., Obora Y., and Tsuji Y. J. Am. Chem. Soc. 126 (2004) 6554-6555
8. Uozumi Y., and Nakao R. Angew. Chem., Int. Ed. 42 (2003) 194-197
9. Sheldon R.A., Arends I.W.C.E., ten Brink G.-J., and Dijksman A. Acc. Chem. Res. 35 (2002) 774-781
10. Nishimura T., Onoue T., Ohe K., and Uemura S. Tetrahedron Lett. 39 (1998) 6011-6014
11. Noyori R., Aoki M., and Sato K. Chem. Commun. (2003) 1977-1986
12. Usui Y., Sato K., and Tanaka M. Angew. Chem., Int. Ed. 42 (2003) 5623-5625
13. Tsuji Y., and Fujihara T. Inorg. Chem. 46 (2007) 1895-1902
14. Tokunaga M., Aoyama H., Kiyosu J., Shirogane Y., Iwasawa T., Obora Y., and Tsuji Y. J. Organomet. Chem. 692 (2007) 472-480
15. Aoyama H., Tokunaga M., Kiyosu J., Iwasawa T., Obora Y., and Tsuji Y. J. Am. Chem. Soc. 127 (2005) 10474-10475
16. Watson M.D., Fechtenkötter A., and Müllen K. Chem. Rev. 101 (2001) 1267-1300
17. Hwang S.W., and Park Y.W. J. Ind. Eng. Chem. 6 (2000) 125-128
18. Park Y.W., and Oh H.H. Bull. Korean Chem. Soc. 18 (1997) 1123-1124
19. Fuchita Y., and Harada Y. Inorg. Chim. Acta 208 (1993) 43-47
20. Wenzel T.T. J. Chem. Soc., Chem. Commun. (1989) 932-933
21. Theissen R.J. J. Org. Chem. 36 (1971) 752-757
22. Reich H.J., Renga J.M., and Reich I.L. J. Am. Chem. Soc. 97 (1975) 5434-5447
23. Nicolaou K.C., Montagnon T., and Baran P.S. Angew. Chem., Int. Ed. 41 (2002) 1386-1389
24. Allyl phosphate was used as a stoichiometric oxidant for this transformation catalyzed by Pd complexes. Shvo Y., and Arisha A.H.I. J. Org. Chem. 63 (1998) 5640-5642
25. Ito Y., Hirao T., and Saegusa T. J. Org. Chem. 43 (1978) 1011-1013
26. Larock R.C., Hightower T.R., Kraus G.A., Hahn P., and Zheng D. Tetrahedron Lett. 36 (1995) 2423-2426
27. Under the reaction condition, facile formation of phosphine oxides was observed.
28. 2. The mixture was stirred at 100 °C for 48 h, and the yield of the product was determined by GC analysis.
29. 12
30. Sharpless K.B., Lauer R.F., and Teranishi A.Y. J. Am. Chem. Soc. 95 (1973) 6137-6139