Synthesis and structural chemistry of arene-ruthenium half-sandwich complexes bearing an oxazolinyl-carbene ligand

Journal of Organometallic Chemistry

Volumn 691, Issue 12, 2006, Pages 2713-2720

  Poyatos, Macarena ^a   Maisse François, Aline ^a   Bellemin Laponnaz, Stéphane ^a   Peris, Eduardo ^b   Gade, Lutz H ^a,c  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b UNIVERSITAT JAUME I   (Spain)

^c UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

Arene complex; Chiral complexes; N heterocyclic carbene; Oxazoline; Ruthenium

Indexed keywords

HYDROGENATION; ISOMERS; NEGATIVE IONS; ORGANIC ACIDS; RUTHENIUM COMPOUNDS; SILVER COMPOUNDS; X RAY DIFFRACTION;

ARENE COMPLEX; CHIRAL COMPLEXES; N-HETEROCYCLIC CARBENE; OXAZOLINE; TRANSMETALLATION;

ORGANOMETALLICS;

EID: 33646344942     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2006.02.008     Document Type: Article

References (50)

1. Öfele K. J. Organomet. Chem. 12 (1968) 42
2. Wanzlick H.W., and Schönherr H.J. Angew. Chem., Int. Ed. 7 (1968) 141
3. Arduengo A.J., Harlow R.L., and Kline M. J. Am. Chem. Soc. 113 (1991) 361
4. Herrmann W.A., Elison M., Fischer J., Köcher C., and Artus G.R.J. Angew. Chem., Int. Ed. 34 (1995) 2371
5. Herrmann W.A., Elison M., Fischer J., Köcher C., and Artus G.R.J. Chem. Eur. J. 2 (1996) 772
6. Herrmann W.A., Goossen L.J., and Spiegler M. J. Organomet. Chem. 547 (1997) 357
7. Reviews:. Herrmann W.A. Angew. Chem., Int. Ed. 41 (2002) 1290
8. Bourissou D., Guerret O., Gabbaï F., and Bertrand G. Chem. Rev. 100 (2000) 39
9. Herrmann W.A., and Köcher C. Angew. Chem., Int. Ed. Engl. 36 (1997) 2162
10. Herrmann W.A., Goossen L.J., Köcher C., and Artus G.R.J. Angew. Chem., Int. Ed. 35 (1996) 2805
11. Enders D., Gielen H., and Beuer K. Tetrahedron: Asymmetry 8 (1997) 3571
12. Powell M.T., Hou D.R., Perry M.C., Cui X.H., and Burgess K. J. Am. Chem. Soc. 123 (2001) 8878
13. César V., Bellemin-Laponnaz S., and Gade L.H. Chem. Soc. Rev. 33 (2004) 619
14. Perry M.C., and Burgess K. Tetrahedron: Asymmetry 14 (2003) 951
15. Gade L.H., César V., and Bellemin-Laponnaz S. Angew. Chem., Int. Ed. 43 (2004) 1014
16. César V., Bellemin-Laponnaz S., Wadepohl H., and Gade L.H. Chem. Eur. J. 11 (2005) 2862
17. Herrmann W.A., Goossen L.J., and Spiegler M. Organometallics 17 (1998) 2162
18. Lowenthal R.E., Abiko A., and Masamune S. Tetrahedron Lett. 31 (1990) 6005
19. Evans D.A., Woerpel K.A., Hinman M.M., and Faul M.M. J. Am. Chem. Soc. 113 (1991) 726
20. Corey E.J., Imai N., and Zhang H.Y. J. Am. Chem. Soc. 113 (1991) 728
21. Müller D., Umbricht G., Weber B., and Pfaltz A. Helv. Chim. Acta 74 (1991) 232
22. For reviews of nitrogen-containing ligands for asymmetric catalysis, see:. Fache F., Schulz E., Lorraine Tommasino M., and Lemaire M. Chem. Rev. 100 (2000) 2159
23. Togni A., and Venanzi L.M. Angew. Chem., Int. Ed. Engl. 33 (1994) 497
24. 2-symmetric bis(oxazolines) in asymmetric catalysis, see:. Ghosh A.K., Mathivanan P., and Cappiello J. Tetrahedron: Asymmetry 9 (1998) 1
25. For a review of applications of oxazoline-containing ligands in asymmetric catalysis, see:. McManus H.A., and Guiry P.J. Chem. Rev. 104 (2004) 4151
26. César V., Bellemin-Laponnaz S., and Gade L.H. Organometallics 21 (2002) 5204
27. César V., Bellemin-Laponnaz S., and Gade L.H. Eur. J. Inorg. Chem. (2004) 3436
28. Schneider N., César V., Bellemin-Laponnaz S., and Gade L.H. J. Organomet. Chem. 690 (2005) 5556
29. Meyers A.I., and Novachek K.A. Tetrahedron Lett. 37 (1996) 1747
30. We also recently reported a very efficient way to synthesize tris-oxazolines using 2-bromooxazoline, see:. Bellemin-Laponnaz S., and Gade L.H. Chem. Commun (2002) 1286
31. Bellemin-Laponnaz S., and Gade L.H. Angew. Chem., Int. Ed. 41 (2002) 3473
32. Wang H.M.J., and Lin I.J.B. Organometallics 17 (1998) 972
33. Lin I.J.B., and Vasam C.S. Comm. Inorg. Chem. 25 (2004) 75
34. Garrison J.C., and Youngs W.J. Chem. Rev. 105 (2005) 3978
35. See for example:. Ciancaleoni G., Bellachioma G., Cardaci G., Ricci G., Ruzziconi R., Zuccaccia D., and Macchioni A. J. Organomet. Chem. 691 (2006) 165
36. Caballero A., Jalon F.A., Manzano B.R., Sauthier M., and Réau R. J. Organomet. Chem. 663 (2002) 118
37. Brunner H. Angew. Chem., Int. Ed. 38 (1999) 1195
38. Brunner H. Eur. J. Inorg. Chem. (2001) 905
39. Brunner H., Weber M., and Zabel M. Coord. Chem. Rev. 242 (2003) 3
40. Enders D., Gielen H., Runsink J., Breuer K., Brode S., and Boehn K. Eur. J. Inorg. Chem. (1998) 913
41. Enders D., and Gielen H. J. Organomet. Chem. 617 (2001) 70
42. Poyatos M., Mas-Marza E., Sanau M., and Peris E. Inorg. Chem. 43 (2004) 1793
43. Poyatos M., Mata J.A., Falomir E., Crabtree R.H., and Peris E. Organometallics 22 (2003) 1110
44. Huang J., Jafarpour L., Hillier A.C., Stevens E.D., and Nolan S.P. Organometallics 20 (2001) 2878
45. For reviews, see:. Naota T., Takaya H., and Murahashi S.I. Chem. Rev. 98 (1998) 2599
46. Palmer M.J., and Wills M. Tetrahedron: Asymmetry 10 (1999) 2045
47. Ishihara K., and Yamamoto H. In: Doyle M.P. (Ed). Advances in Catalytic Processes vol. 1 (1995), JAI Press, London 29
48. Bennett M.A., and Smith A.K. J. Chem. Soc., Dalton Trans. (1974) 233
49. Nonius openmolen, Interactive Structure Solution, Delft, 1997.
50. Cromer D.T., and Waber J.T. International Tables for X-ray Crystallography (1974), The Kynoch Press, Birmingham