Chiral porphyrin complexes of cobalt(II) and ruthenium(II) in catalytic cyclopropanation and amination reactions

Inorganica Chimica Acta

Volumn 359, Issue 9, 2006, Pages 2924-2932

  Caselli, Alessandro ^a   Gallo, Emma ^a   Ragaini, Fabio ^a   Ricatto, Federica ^a   Abbiati, Giorgio ^a   Cenini, Sergio ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

Amination reactions; Chiral porphyrins; Cobalt; Cyclopropanation reactions; Ruthenium

Indexed keywords

AMINES; AROMATIC HYDROCARBONS; CATALYST ACTIVITY; COBALT; COBALT COMPOUNDS; METAL COMPLEXES; PORPHYRINS; RUTHENIUM; SYNTHESIS (CHEMICAL); TRANSITION METALS;

AMINATION REACTION; ASYMMETRIC TRANSFER; CATALYTIC CYCLOPROPANATION; CYCLOPROPANATION REACTION; DIASTEREO- AND ENANTIOSELECTIVITY; PORPHYRIN COMPLEXES; PROCHIRAL OLEFINS; UNSATURATED HYDROCARBONS;

RUTHENIUM COMPOUNDS;

EID: 33646514856     PISSN: 00201693     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ica.2005.11.020     Document Type: Article

References (49)

1. Blaser H.-U., Pugin B., and Spindler F. J. Mol. Catal. A: Chem. 231 (2005) 1
2. Blaser H.-U., and Schmidt E. Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions (2003), Wiley-VCH, Weinheim
3. Ezhova M.B., and James B.R. In: Simandi L. (Ed). Advances in Catalytic Activation of Dioxygen by Metal Complexes (2002), Kluwer Academic, Dordrecht, The Netherlands 1-77
4. In: Sheldon R.A. (Ed). Metalloporphyrins in Catalytic Oxidations (1994), Marcel Dekker, New York
5. In: Montanari F., and Casella L. (Eds). Metalloporphyrins Catalyzed Oxidations (1994), Kluwer Academic, Dordrecht, The Netherlands
6. Groves J.T., and Myers R.S. J. Am. Chem. Soc. 105 (1983) 5791
7. Simonneaux G., and Le Maux P. Coord. Chem. Rev. 228 (2002) 43
8. Marchon J.-C., and Ramasseul R. Porphyrin Handbook 11 (2003) 75
9. Rose E., Ren Q.-Z., and Andrioletti B. Chem. Eur. J. 10 (2004) 224
10. Rose E., Quelquejeu M., Pandian R.P., Lecas-Nawrocka A., Vilar A., Ricart G., Collman J.P., Wang Z., and Straumanis A. Polyhedron 19 (2000) 581
11. Barry J.F., Campbell L., Smith D.W., and Kodadek T. Tetrahedron 53 (1997) 7753
12. Collman J.P., Zhang X., Lee V.J., Uffelman E.S., and Brauman J.I. Science 261 (1993) 1404
13. Chen Y., Fields K.B., and Zhang X.P. J. Am. Chem. Soc. 126 (2004) 14718
14. O'Malley S., and Kodadek T. J. Am. Chem. Soc. 111 (1989) 9116
15. Rose E., Soleilhavoup M., Christ-Tomasino L., Moreau G., Collman J.P., Quelquejeu M., and Straumanis A. J. Org. Chem. 63 (1998) 2042
16. Berkessel A., Kaiser P., and Lex J. Chem. Eur. J. 9 (2003) 4746
17. Zhang R., Yu W.-Y., Sun H.-Z., Liu W.-S., and Che C.-M. Chem. Eur. J. 8 (2002) 2495
18. Nakagawa H., Sei Y., Yamaguchi K., Nagano T., and Higuchi T. Tetrahedron: Asymmetry 15 (2004) 3861
19. Halterman R.L., and Mei X. Tetrahedron Lett. 37 (1996) 6291
20. Perollier C., Mazzanti M., Simonato J.-P., Launay F., Ramasseul R., and Marchon J.-C. Eur. J. Org. Chem. (2000) 583
21. Gazeau S., Pecaut J., Haddad R., Shelnutt J.A., and Marchon J.-C. Eur. J. Inorg. Chem. (2002) 2956
22. Veyrat M., Maury O., Faverjon F., Over D.E., Ramasseul R., Marchon J.C., Turowska-Tyrk I., and Scheidt W.R. Angew. Chem. Int. Ed. Engl. 33 (1994) 220
23. Johnstone R.A.W., Nunes M.L.P.G., Pereira M.M., d'A Rocha Gonsalves A.M., and Serra A.C. Heterocycles 43 (1996) 1423
24. Adler A.D., Longo F.R., and Varadi V. Inorg. Synth. 16 (1976) 213
25. Eady C.R., Jackson P.F., Johnson B.F.G., Lewis J., Malatesta M.C., McPartlin M., and Nelson W.J.H. J. Chem. Soc., Dalton Trans. (1980) 383
26. Ribaldone G., Caprara G., and Borsotti G. Chim. Ind. 50 (1968) 1200
27. Cenini S., Tollari S., Penoni A., and Cereda C. J. Mol. Catal. A: Chem. 137 (1999) 135
28. Fantauzzi S., Gallo E., Caselli A., Ragaini F., Macchi P., Casati N., and Cenini S. Organometallics 24 (2005) 4710
29. Niimi T., Uchida T., Irie R., and Katsuki T. Adv. Synth. Catal. 343 (2001) 79
30. Lindsey J.S., Schreiman I.C., Hsu H.C., Kearney P.C., and Marguerettaz A.M. J. Org. Chem. 52 (1987) 827
31. For a recent example of a MM study of metalloporphyrins see. Gruden-Pavlovic M., Grubisic S., and Niketic S.R.J. Inorg. Biochem. 98 (2004) 1293
32. Hypercube, 1115 NW 4th Street, Gainesville, FL 32601 USA. Available from: .
33. Scheidt W.R., and Turowska-Tyrk I. Inorg. Chem. 33 (1994) 1314
34. Chen B.M.L., and Tulinsky A. J. Am. Chem. Soc. 94 (1972) 4144
35. Gallo E., Caselli A., Ragaini F., Fantauzzi S., Masciocchi N., Sironi A., and Cenini S. Inorg. Chem. 44 (2005) 2039
36. S. Cenini, E. Gallo, A. Caselli, F. Ragaini, S. Fantauzzi, C. Piangiolino, Coord. Chem. Rev., in press.
37. Ragaini F., Penoni A., Gallo E., Tollari S., Li Gotti C., Lapadula M., Mangioni E., and Cenini S. Chem. Eur. J. 9 (2003) 249
38. Cenini S., Gallo E., Penoni A., Ragaini F., and Tollari S. Chem. Commun. (2000) 2265
39. S. Cenini, E. Gallo, A. Caselli, F. Ragaini, S. Fantauzzi, C. Piangiolino, manuscript in preparation.
40. Brase S., Gil C., Knepper K., and Zimmermann V. Angew. Chem., Int. Ed. 44 (2005) 5188
41. In: Patai S. (Ed). The Chemistry of the Azido Group (1971), Interscience Publishers, London
42. Mansuy D. Pure Appl. Chem. 62 (1990) 741
43. Liang J.-L., Huang J.-S., Yu X.-Q., Zhu N., and Che C.-M. Chem. Eur. J. 8 (2002) 1563
44. Caselli A., Gallo E., Ragaini F., Oppezzo A., and Cenini S. J. Organomet. Chem. 690 (2005) 2142
45. Omura K., Uchida T., Irie R., and Katsuki T. Chem. Commun. (2004) 2060
46. Omura K., Murakami M., Uchida T., Irie R., and Katsuki T. Chem. Lett. 32 (2003) 354
47. Murakami M., Uchida T., and Katsuki T. Tetrahedron Lett. 42 (2001) 7071
48. Tamura Y., Uchida T., and Katsuki T. Tetrahedron Lett. 44 (2003) 3301
49. Penoni A., Wanke R., Tollari S., Gallo E., Musella D., Ragaini F., Demartin F., and Cenini S. Eur. J. Inorg. Chem. (2003) 1452