A catalytic process for the selective oxidation of alcohols by copper (II) complexes

Inorganic Chemistry Communications

Volumn 14, Issue 5, 2011, Pages 690-693

  Ramakrishna, Dileep ^a   Bhat, Badekai Ramachandra ^a  

^a NATIONAL INSTITUTE OF TECHNOLOGY KARNATAKA   (India)

Author keywords

Catalytic oxidation; Copper (II) complexes; Periodic acid; Schiff base

Indexed keywords

EID: 79954425145     PISSN: 13877003     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.inoche.2011.02.007     Document Type: Article

References (39)

1. R.A. Sheldon, and J.K. Kochi Metal-Catalyzed Oxidations of Organic Compounds 1981 Academic Press New York
2. M. Musawir, P.N. Davey, G. Kelly, and I.V. Kozhevnikov Chem. Commun. 2003 1414
3. W.S. Trahanovsky A.T. Blomquist, H. Wasserman, Oxidation in Organic Chemistry 1978 Academic Press New York
4. B.-Z. Zhan, M.A. White, T.-K. Sham, J.A. Pincock, R.J. Doucet, K.V. Ramana Rao, K.N. Robertson, and T. Stanley Cameron J. Am. Chem. Soc. 125 2003 2195
5. H. Ji, T. Mizugaki, K. Ebitani, and K. Kaneda Tetrahedron Lett. 43 2002 7179
6. P. Gamez, P.G. Aubel, W.L. Driessen, and J. Reedijk Chem. Soc. Rev. 30 2001 376
7. I.P. Skibida, and A.M. Sakharov Catal. Today 27 1996 187
8. A. Wolfson, S. Wuyts, D.E. De Vos, I.F.J. Vankelecom, and P.A. Jacobs Tetrahedron Lett. 43 2002 8107
9. J.W. Li, W. Sun, L.W. Xu, C.G. Xia, and H.W. Wang Chinese Chem. Lett. 15 2004 1437
10. B.S. Chhikara, S. Tehlan, and A. Kumar Synlett 2005 63
11. G. Bianchini, M. Crucianelli, F. de Angelis, V. Neri, and R. Saladino Tetrahedron Lett. 46 2005 2427
12. A. Kumar, N. Jain, and S.M.S. Chauhan Synlett 2007 411
13. J. Nan, and J.R. Arthur Tetrahedron Lett. 48 2007 273
14. I.E. Markó, P.R. Giles, M. Tsukazaki, I. Chellé-Regnaut, A. Gautier, S.M. Brown, and C.J. Urch J. Org. Chem. 64 1999 2433
15. Y. Wang, J.L. DuBois, B. Hedman, K.O. Hodgson, and T.D.P. Stack Science 279 1998 537
16. P. Chaudhuri, M. Hess, U. Flörke, and K. Wieghardt Angew. Chem. Int. Ed. 37 1998 2217
17. G. Ragagnin, B. Betzemeier, S. Quici, and P. Knochel Tetrahedron 58 2002 3985
18. I.A. Ansari, and R. Gree Org. Lett. 4 2002 1507
19. G. Nageswara Rao, Ch. Janardhana, K. Pasupathy, and P. Mahesh Kumar Indian J. Chem. B 39 2000 151
20. A. Sarkar, and S. Pal Polyhedron 25 2006 1689
21. To a solution of [CuCl2(PPh3)2] (0.2 mmol) in alcohol (20 mL) the corresponding Schiff base ligand (0.2 mmol) was added. The mixture was refluxed for 3 h. The solvent was evaporated to 1/3rd and n-hexane was added to separate the solid complex. The complex was filtered, washed with ethanol and then with hexane and dried in vacuo. The formation of complex was checked by TLC.
22. R.M. Claramount, I. Forfar, P. Cabildo, J. Lafuente, J. Barbera, R. Giménez, and J. Elguero Heterocycles 51 1999 751
23. S.A. Sallam, and A.S. Orabi Egypt J. Chem. 47 2004 383
24. C. Condorelli, I. Fragala, S. Giuffrida, and A. Cassol Z. Anorg. Allg. Chem. 412 1975 251
25. F. Dianzhong, and W. Bo Transit. Met. Chem. 18 1993 101
26. R. Karvembu, and K. Natarajan Polyhedron 21 2002 1721
27. R. Karvembu, and K. Natarajan Polyhedron 21 2002 219
28. M. Muthu Tamizh, K. Mereiter, K. Kirchner, B.R. Bhat, and R. Karvembu Polyhedron 28 2009 2157
29. V. Philip, V. Suni, M.R.P. Kurup, and M. Nethaji Polyhedron 23 2004 1225
30. D. Ramakrishna, B. Ramachandra Bhat, and R. Karvembu Catal. Commun. 11 2010 498
31. B.V. Patel, K. Desai, and T. Thaker Synth. React. Inorg. Met. Org. Chem. 19 1989 391
32. F.J. Barros-Garcia, F. Luna-Giles, M.A. Maldonado-Rogado, and E. Vinuelas-Zahinos Polyhedron 24 2005 2972
33. N. Raman, A. Kulandaisamy, and C. Thangaraja Trans. Met. Chem. 28 2003 29
34. R. Abraham, and K.K.M. Yusuf J. Mol. Catal. A 198 2003 175
35. D. Datta, and A. Chakravorty Inorg. Chem. 22 1983 1085
36. J. Heinze Angew. Chem. Int. Ed Engl. 23 1984 831
37. A solution of copper complex (0.01 mmol) in 20 mL acetonitrile was added to the solution of substrate (1 mmol) and H5IO6 (1 mmol). The mixture was stirred at 70 °C. At the requisite times aliquots of the reaction mixture were removed and the alcohol and aldehyde/ketone extracted with ether. The ether solution was then analyzed by GC.
38. The reaction product analysis was carried out using gas chromatography (GC) (Shimadzu 2014, Japan); the instrument has a 5% diphenyl and 95% dimethyl siloxane Restek capillary column (30 m length and 0.25 mm diameter) and a flame ionization detector (FID). Nitrogen gas was used as the carrier gas. The retention times for different compounds were determined by injecting commercially available compounds under identical gas chromatography conditions. The oxidation products are commercially available, and were identified by GC co-injection with authentic samples.
39. S. Velusamy, A. Srinivasan, and T. Punniyamurthy Tetrahedron Lett. 47 2006 923