Highly efficient C-H insertion reactions of hydrogen peroxide catalyzed by homogeneous and heterogeneous methyltrioxorhenium systems in ionic liquids

Tetrahedron Letters

Volumn 46, Issue 14, 2005, Pages 2427-2432

  Bianchini, Gianluca ^a   Crucianelli, Marcello ^a   De Angelis, Francesco ^a   Neri, Veronica ^b   Saladino, Raffaele ^b  

^a UNIVERSITY OF L'AQUILA   (Italy)

^b UNIVERSITY OF TUSCIA   (Italy)

Author keywords

C H insertion reaction; Heterogeneous catalysis; Hydrogen peroxide; Ionic liquid; Methyltrioxorhenium

Indexed keywords

CARBON; FLUORINE DERIVATIVE; HYDROGEN; HYDROGEN PEROXIDE; ION; NITROGEN DERIVATIVE; POLYSTYRENE DERIVATIVE; PYRIDINE DERIVATIVE; RHENIUM COMPLEX; SOLVENT;

ARTICLE; CATALYST; CHEMICAL ENVIRONMENT; CHEMICAL REACTION; INTERMETHOD COMPARISON; LIQUID; MICROENCAPSULATION; SUBSTITUTION REACTION;

EID: 17744397730     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.02.056     Document Type: Article

References (49)

1. J.S. Wilkes J. Mol. Catal. A: Chem. 214 2004 11 17
2. S.A. Forsyth, J.M. Pringle, and D.R. MacFarlane Aust. J. Chem. 57 2004 113 119
3. J. Dupont, R.F. de Souza, and P.A.Z. Suarez Chem. Rev. 102 2002 3667 3691
4. H. Zhao, and S.V. Malhotra Aldrichim. Acta 35 2002 75 83
5. H. Olivier-Bourbigou, and L. Magna J. Mol. Catal. A: Chem. 182-183 2002 419 437
6. M.C.A. van Vliet, I.W.C.E. Arends, and R.A. Sheldon Chem. Commun. 1999 821 822
7. R.T. Baker, and W. Tumas Science 284 1999 1427
8. D. Zhao, M. Wu, Y. Kou, and E. Min Catal. Today 74 2002 157 189
9. R. Sheldon Chem. Commun. 2001 2399
10. T. Welton Chem. Rev. 99 1999 2071
11. M.J. Earle, P.B. McCormac, and K.R. Seddon Green Chem. 1 1999 23
12. Y. Chauvin, L. Mussman, and H. Olivier Angew. Chem., Int. Ed. Eng. 34 1995 2698
13. G.S. Owens, and M.M. Abu-Omar Chem. Commun. 2000 1165 1166
14. P. Bonhôte, A.-P. Dias, N. Papageorgiou, K. Kalyanasundaram, and M. Grätzel Inorg. Chem. 35 1996 1168 1178
15. For some recent examples of catalytic oxidation in ionic liquids: F.E. Kühn, J. Zhao, M. Abrantes, W. Sun, C.A.M. Afonso, L.C. Branco, I.S. Gonçalves, M. Pillinger, and C.C. Romão Tetrahedron Lett. 46 2005 47 52
16. A.A. Valente, Ž Petrovski, L.C. Branco, C.A.M. Afonso, M. Pillinger, A.D. Lopes, C.C. Romão, C.D. Nunes, and I.S. Gonçalves J. Mol. Catal. A: Chem. 218 2004 5 11
17. Z. Li, and C.-G. Xia J. Mol. Catal. A: Chem. 214 2004 95 101
18. K.-H. Tong, K.-Y. Wong, and T.H. Chan Org. Lett. 5 2003 3423 3425
19. J. Peng, F. Shi, Y. Gu, and Y. Deng Green Chem. 5 2003 224 226
20. K.A. Srinivas, A. Kumar, and S.M.S. Chauhan Chem. Commun. 2002 2456 2457
21. 2 oxidation of hydrocarbons see: G.B. Shul'pin C. R. Chimie 6 2003 163 178
22. G.V. Nizova, C. Bolm, S. Ceccarelli, C. Pavan, and G.B. Shul'pin Adv. Synth. Catal. 344 2002 899 905
23. For general reviews on MTO chemistry: F.E. Kühn, A. Scherbaum, and W.A. Herrmann J. Organomet. Chem. 689 2004 4149 4164
24. G.S. Owens, J. Arias, and M.M. Abu-Omar Catal. Today 55 2000 317 363
25. C.C. Romão, F.E. Kühn, and W.A. Herrmann Chem. Rev. 97 1997 3197 3246
26. W.A. Herrmann, R.W. Fischer, W. Scherer, and M.U. Rauch Angew. Chem., Int. Ed. Engl. 32 1993 1157 1160
27. G.S. Owens, and M.M. Abu-Omar J. Mol. Catal. A: Chem. 187 2002 215 225
28. G.S. Owens, A. Durazzo, and M.M. Abu-Omar Chem. Eur. J. 8 2002 3053 3059
29. R. Bernini, A. Coratti, G. Fabrizi, and A. Coggiamani Tetrahedron Lett. 44 2003 8991 8994
30. 4] was measured using diethyl ether as mobile phase, with a concomitant dramatic decrease of the catalytic activity
31. G. Bianchini, M. Crucianelli, F. De Angelis, V. Neri, and R. Saladino Tetrahedron Lett. 45 2004 2351 2353
32. R. Saladino, E. Mincione, O.A. Attanasi, and P. Filippone Pure Appl. Chem. 75 2003 261 268
33. R. Saladino, V. Neri, A.R. Pelliccia, and E. Mincione Tetrahedron 59 2003 7403 7408
34. R. Saladino, V. Neri, E. Mincione, and P. Filippone Tetrahedron 58 2002 8493 8500
35. R. Saladino, V. Neri, A.R. Pelliccia, R. Caminiti, and C. Sadun J. Org. Chem. 67 2002 1323 1332
36. 14. In summary, MTO (256 mg, 1.0 mmol) was added to a suspension of the appropriate resin (1.0 g) in ethanol (4 mL). The mixture was stirred during 1 h by a magnetic stirring. The solvent was removed by filtration, and the catalyst was washed with ethyl acetate and finally dried under high vacuum
37. The reaction mixtures were analyzed by a Hewlett Packard 6890 Series gas chromatograph equipped with a FID, using a 30 m × 0.32 mm × 0.25 μm film thickness (cross-linked 5% phenylmethylsiloxane) column and nitrogen as carrier gas. The identification of the peaks by GC-MS has been performed by means of a Varian 2000 GC-MS instrument, using the same column. Yields and conversions of the reactions have been quantified using n-octane as internal standard, or when necessary, after chromatographic purification
38. W. Adam, C.R. Saha-Möller, M. Shimizu, and W.A. Herrmann J. Mol. Catal. A: Chem. 97 1995 15 20
39. S.M. Nabavizadeh Inorg. Chem. 42 2003 4204
40. W.-D. Wang, and J.H. Espenson J. Am. Chem. Soc. 120 1998 11335 11341
41. F.E. Kühn, A.M. Santos, P.W. Roesky, E. Herdtweck, W. Scherer, P. Gisdakis, I.V. Yudanov, C. Di Valentin, and N. Rosch Chem. Eur. J. 5 1999 3603 3615
42. W.A. Herrmann, J.D.G. Correira, M.U. Rauch, G.R.J. Artus, and F.E. Kühn J. Mol. Catal. A: Chem. 118 1997 33 45
43. For some recent examples of improved transformations in ionic liquids with respect to molecular solvents see: W. Sun, and F.E. Kühn Tetrahedron Lett. 45 2004 7415 7418
44. H.-P. Nguyen, S. Znifeche, and M. Baboulene Synth. Commun. 34 2004 2085 2093
45. Y. Hu, Z.-C. Chen, Z.-G. Le, and Q.-G. Zheng Synth. Commun. 34 2004 3801 3806
46. P. Wasserscheid T. Welton Ionic Liquids in Synthesis 2003 Wiley-VCH Weinheim
47. P. Wasserscheid, M. Sesing, and W. Korth Green Chem. 4 2002 134 138
48. D.W. Kim, C.E. Song, and D.Y. Chi J. Am. Chem. Soc. 124 2002 10278 10279
49. R.W. Murray, and D. Gu J. Chem. Soc., Perkin Trans. 2 1994 451 453