Structural characterization and catalytic activity of the rhodium-carbene complex Rh(PPh3)2(IMes)Cl (IMes = bis(1,3-(2,4,6-trimethylphenyl)imidazol-2-ylidene)

Journal of Organometallic Chemistry

Volumn 658, Issue 1-2, 2002, Pages 126-131

  Grasa, Gabriela A ^a   Moore, Zakhia ^a   Martin, Kenneth L ^a   Stevens, Edwin D ^a   Nolan, Steven P ^a   Paquet, Valérie ^b   Lebel, Hélène ^b  

^a UNIVERSITY OF NEW ORLEANS   (United States)

^b UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

Catalytic activity; Rhodium carbene complexes; Structural characterization

Indexed keywords

ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; CARBENE; RHODIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL INTERACTION; CHEMICAL PARAMETERS; CHEMICAL PROCEDURES; CHEMICAL REACTION; COMPLEX FORMATION; CONTROLLED STUDY; CRYSTAL STRUCTURE; ROOM TEMPERATURE; STRUCTURE ANALYSIS;

EID: 0037120311     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(02)01638-8     Document Type: Article

References (56)

1. J.A. Osborn, F.H. Jardine, J.F. Young, G. Wilkinson, J. Chem. Soc. Sect. A (1966) 1711;
2. F.H. Jardine, J.A. Osborn, G. Wilkinson, J. Chem. Soc. Sect. A (1967) 1574;
3. S. Montelatici, A. van der Ent, J.A. Osborn, G. Wilkinson, J. Chem. Soc. Sect. A (1968) 1054.
4. R.N. Haszeldine, R.V. Parish, D.J. Parry, J. Organomet. Chem. 9 (1967) 13.
5. D. Männig, H. Nöth, Angew. Chem. Int. Ed. Engl. 24 (1985) 878;
6. D.A. Evans, G.C. Fu, A.H. Hoveyda, J. Am. Chem. Soc. 114 (1992) 6671;
7. D.A. Evans, G.C. Fu, B.A. Anderson, J. Am. Chem. Soc. 114 (1992) 6679.
8. For directed hydroboration see: (a) J.A. Brinkman, T.T. Nguyen, J.R. Sowa Jr., Org. Lett. 2 (2000) 981;
9. D.A. Evans, G.C. Fu, J. Am. Chem. Soc. 113 (1991) 4042; For directed hydrogenation see:
10. G. Stork, D.E. Kahne, J. Am. Chem. Soc. 105 (1983) 1072;
11. R.H. Crabtree, M.W. Davis, Organometallics 2 (1983) 681.
12. H. Lebel, V. Paquet, C. Proulx, Angew. Chem. Int. Ed. Engl. 40 (2001) 2887.
13. M. Regitz, Angew. Chem. Int. Ed. Engl. 35 (1996) 725;
14. A.J. Arduengo, III, R. Krafczyk, Chem Zeit. 32 (1998) 6;
15. W.A. Hermann, C. Köcher, Angew. Chem. Int. Ed. Engl. 31 (1997) 2163;
16. J.E.L. Dullius, P.A.Z. Suarez, S. Einloft, R.F. de Souza, J. Dupont, J. Fischer, A. De Cian, Organometallics 17 (1998) 815;
17. A.J. Arduengo, III, Acc. Chem. Res. 32 (1999) 913.
18. Applications of phosphine ligands in homogeneous catalysis: (a) G.W. Parshall, S. Ittel, Homogenous Catalysis, John Wiley and Sons, New York, 1992;
19. L.H. Pignolet (Ed.), Homogenous Catalysis with Metal Phosphine Complexes, Plenum, New York, 1983.
20. J. Huang, S.P. Nolan, J. Am. Chem. Soc. 121 (1999) 9889;
21. H.M. Lee, S.P. Nolan, Org. Lett. 2 (2000) 1307;
22. G.A. Grasa, S.P. Nolan, Org. Lett. 3 (2001) 119;
23. C. Zhang, J. Huang, M.L. Trudell, S.P. Nolan, J. Org. Chem. 64 (1999) 3804;
24. V.P.W. Böhm, C.W.K. Gstöttmayer, T. Weskamp, W.A. Herrmann, J. Orgamomet. Chem. 595 (2000) 186;
25. D. McGuiness, K.J. Cavell, Organometallics 19 (2000) 741;
26. S. Gründemann, M. Albrecht, J.A. Loch, J.W. Faller, R.H. Crabtree, Organometallics 20 (2001) 5485;
27. S. Caddick, F.G.N. Cloke, J.K.B. Clentsmith, G.P.B. Hitchcock, D. McKerrecher, L.R. Titcomb, M.R.V. Williams, J. Organomet. Chem. 617-618 (2001) 635.
28. J. Huang, G.A. Grasa, S.P. Nolan, Org. Lett. 1 (1999) 1307;
29. G.A. Grasa, M.S. Viciu, J. Huang, S.P. Nolan, J. Org. Chem. 66 (2001) 7729;
30. S.R. Stauffer, S. Lee, J.P. Stambuli, S.I. Hauck, J.F. Hartwig, Org. Lett. 2 (2000) 1423.
31. A.C. Chen, L. Ren, A. Decken, C.M. Crudden, Organometallics 19 (2000) 3459.
32. J. Huang, E.D. Stevens, S.P. Nolan, J.L. Petersen, J. Am. Chem. Soc. 121 (1999) 2674;
33. M. Scholl, T.M. Trnka, J.P. Morgan, R.H. Grubbs, Tetrahedron Lett. 40 (1999) 2247;
34. L. Ackermann, A. Fürstner, T. Weskamp, F.J. Kohl, W.A. Herrmann, Tetrahedron Lett. 40 (1999) 4787;
35. J. Huang, H.-J. Schanz, E.D. Stevens, S.P. Nolan, Organometallics 18 (1999) 2370;
36. L. Jafarpour, H.-J. Schanz, E.D. Stevens, S.P. Nolan, Organometallics 18 (1999) 5416;
37. M. Scholl, S. Ding, C.W. Lee, R.H. Grubbs, Org. Lett. 1 (1999) 953;
38. A.K. Chatterjee, R.H. Grubbs, Org. Lett. 1 (2000) 1751;
39. D. Bourissou, O. Guerret, F.P. Gabbaï, G. Bertrand, Chem. Rev. 100 (2000) 39 (and references therein);
40. T.M. Trnka, R.H. Grubbs, Acc. Chem. Res. 34 (2001) 18.
41. M.F. Lappert, J. Organomet. Chem. 358 (1988) 185;
42. M.J. Doyle, M.F. Lappert, P.L. Pye, P. Terreros, J. Chem. Soc. Dalton Trans. (1984) 2355;
43. M.F. Lappert, R.K. Maskell, J. Organomet. Chem. 264 (1984) 217.
44. Y. Ohtani, M. Fujimoto, A. Yamagishi, Bull. Chem. Soc. Jpn. 49 (1976) 1871.
45. V.G. Albano, P. Bellon, M. Sansoni, J. Chem. Soc. Sect. A 15 (1971) 2420;
46. M.J. Bennett, P.B. Donaldson, Inorg. Chem. 16 (1971) 655.
47. R.H. Crabtree, H. Felkin, G.E. Morris, J. Organomet. Chem. 135 (1977) 205;
48. R.H. Crabtree, G.E. Morris, J. Organomet. Chem. 135 (1977) 395;
49. R.H. Crabtree, Acc. Chem. Res. 12 (1979) 331;
50. R.H. Crabtree, H. Felkin, T. Fillebeen-Khan, G.E. Morris, J. Organomet. Chem. 168 (1979) 183;
51. H.-M. Lee, T. Jiang, E.D. Stevens, S.P. Nolan, Organometallics 20 (2001) 1255.
52. C. Widauer, H. Grützmacher, T. Ziegler, Organometallics 19 (2000) 2097.
53. H. Lebel, V. Paquet, Unpublished results.
54. Those reaction conditions required large amount of trimethylsilyldiazomethane ( > 2.0 equivalents) to produce the olefin quantitatively. From a practical point of view, the standard reaction conditions will provide better overall yield, even if higher temperatures are required.
55. H.-W. Wanzlick, Angew. Chem. Int. Ed. Engl. 1 (1962) 75;
56. A.J. Arduengo, III, H.V.R. Dias, R.L. Harlow, M. Kline, J. Am. Chem. Soc. 114 (1992) 5530.