Nickel(II) complexes with bifunctional phosphine-imidazolium ligands and their catalytic activity in the Kumada-Corriu coupling reaction

Journal of Organometallic Chemistry

Volumn 691, Issue 3, 2006, Pages 433-443

  Wolf, Joffrey ^a   Labande, Agnès ^a   Daran, Jean Claude ^a   Poli, Rinaldo ^a  

^a LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

Author keywords

Bifunctional ligands; Imidazolium; Kumada Corriu reaction; Nickel(II); Phosphine

Indexed keywords

CATALYSTS; NICKEL; PHOSPHORUS; REACTION KINETICS; STOICHIOMETRY; X RAY CRYSTALLOGRAPHY;

BIFUNCTIONAL LIGANDS; IMIDAZOLIUM; KUMADA-CORRIU REACTION; NICKEL(II); PHOSPHINE;

COMPLEXATION;

EID: 29344475927     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2005.09.010     Document Type: Article

References (63)

1. D. Bourissou, O. Guerret, F.P. Gabbai, and G. Bertrand Chem. Rev. 100 2000 39
2. W.A. Herrmann Angew. Chem., Int. Ed. Engl. 41 2002 1290
3. K.J. Cavell, and D.S. McGuinness Coord. Chem. Rev. 248 2004 671
4. C.L. Yang, H.M. Lee, and S.P. Nolan Org. Lett. 3 2001 1511
5. L.G. Bonnet, R.E. Douthwaite, R. Hodgson, J. Houghton, B.M. Kariuki, and S. Simonovic J. Chem. Soc., Dalton Trans. 2004 3528
6. B.E. Ketz, A.P. Cole, and R.M. Waymouth Organometallics 23 2004 2835
7. S. Roland, M. Audouin, and P. Mangeney Organometallics 23 2004 3075
8. M.S. Viciu, O. Navarro, R.F. Germaneau, R.A. Kelly, W. Sommer, N. Marion, E.D. Stevens, L. Cavallo, and S.P. Nolan Organometallics 23 2004 1629
9. N. Tsoureas, A.A. Danopoulos, A.A.D. Tulloch, and M.E. Light Organometallics 22 2003 4750
10. A. Fürstner, G. Seidel, D. Kremzow, and C.W. Lehmann Organometallics 22 2003 907
11. K. Selvakumar, A. Zapf, and M. Beller Org. Lett. 4 2002 3031
12. M.G. Gardiner, W.A. Herrmann, C.P. Reisinger, J. Schwarz, and M. Spiegler J. Organomet. Chem. 572 1999 239
13. H.M. Sun, Q. Shao, D.M. Hu, W.F. Li, Q. Shen, and Y. Zhang Organometallics 24 2005 331
14. X. Wang, S. Liu, and G.X. Jin Organometallics 23 2004 6002
15. S. Winston, N. Stylianides, A.A.D. Tulloch, J.A. Wright, and A.A. Danopoulos Polyhedron 23 2004 2813
16. R. Sawaki, Y. Sato, and M. Mori Org. Lett. 6 2004 1131
17. J. Louie, J.E. Gibby, M.V. Farnworth, and T.N. Tekavec J. Am. Chem. Soc. 124 2002 15188
18. D.S. McGuinness, W. Mueller, P. Wasserscheid, K.J. Cavell, B.W. Skelton, A.H. White, and U. Englert Organometallics 21 2002 175
19. R.E. Douthwaite, M.L.H. Green, P.J. Silcock, and P.T. Gomes Organometallics 20 2001 2611
20. R.E. Douthwaite, D. Haussinger, M.L.H. Green, P.J. Silcock, P.T. Gomes, A.M. Martins, and A.A. Danopoulos Organometallics 18 1999 4584
21. V.P.W. Böhm, T. Weskamp, C.W.K. Gstöttmayr, and W.A. Herrmann Angew. Chem., Int. Ed. Engl. 39 2000 1602
22. W.A. Herrmann, G. Gerstberger, and M. Spiegler Organometallics 16 1997 2209
23. T. Focken, G. Raabe, and C. Bolm Tetrahedron: Asymmery 15 2004 1693
24. E. Mas-Marza, M. Poyatos, M. Sanau, and E. Peris Inorg. Chem. 43 2004 2213
25. M. Poyatos, E. Mas-Marza, J.A. Mata, M. Sanau, and E. Peris Eur. J. Inorg. Chem. 2003 1215
26. H. Seo, H. Park, B.Y. Kim, J.H. Lee, S.U. Son, and Y.K. Chung Organometallics 22 2003 618
27. M.C. Perry, X.H. Cui, M.T. Powell, D.R. Hou, J.H. Reibenspies, and K. Burgess J. Am. Chem. Soc. 125 2003 113
28. C. Bolm, M. Kesselgruber, and G. Raabe Organometallics 21 2002 707
29. B. Cetinkaya, I. Özdemir, and P.H. Dixneuf J. Organomet. Chem. 534 1997 153
30. W.A. Herrmann, C. Köcher, L.J. Gooßen, and G.R.J. Artus Chem. Eur. J. 2 1996 1627
31. E. Bappert, and G. Helmchen Synlett 2004 1789
32. S. Gischig, and A. Togni Organometallics 23 2004 2479
33. Z. Fei, D. Zhao, T.J. Geldbach, R. Scopelliti, and P.J. Dyson Chem. Eur. J. 10 2004 4886
34. C.S. Consorti, P.A.Z. Suarez, R.F.d. Souza, R.A. Burrow, D.H. Farrar, A.J. Lough, W. Loh, L.H.M.d. Silva, and J. Dupont J. Phys. Chem. B 109 2005 4341
35. M.C. Smith, S.C. Davies, D.L. Hughes, and D.J. Evans Acta Crystallogr. Sect. E 57 2001 m509
36. M. Brenndorfer, H.A. Brune, and T. Debaerdemaeker Z. Naturforsch. Teil B 40 1985 357
37. L.R. Hanton, and P.R. Raithby Acta Crystallogr. Sect. B 36 1980 2417
38. E.C. Alyea, A. Costin, G. Ferguson, G.T. Fey, R.G. Goel, and R.J. Restivo J. Chem. Soc., Dalton Trans. 1975 1294
39. E.C. Alyea, G. Ferguson, M. Parvez, and J.E. Davies Cryst. Struct. Commun. 11 1982 1713
40. F.A. Cotton, and G. Wilkinson Advanced Inorganic Chemistry 1988 Wiley New York
41. A.A. Danopoulos, S. Winston, T. Gelbrich, M.B. Hursthouse, and R.P. Tooze J. Chem. Soc., Chem. Commun. 2002 482
42. F.E. Hahn, M. Paas, D.L. Van, and T. Lügger Angew. Chem., Int. Ed. Engl. 42 2003 5243
43. Z. Shi, and R.P. Thummel J. Org. Chem. 60 1995 5935
44. T.A. Taton, and P. Chen Angew. Chem., Int. Ed. Engl. 35 1996 1011
45. K. Tamao, K. Sumitani, and M. Kumada J. Am. Chem. Soc. 94 1972 4374
46. R.J.P. Corriu, and J.P. Masse J. Chem. Soc., Chem. Commun. 1972 144
47. K. Tamao, Y. Kiso, K. Sumitani, and M. Kumada J. Am. Chem. Soc. 94 1972 9268
48. K. Tamao, S. Kodama, I. Nakajima, M. Kumada, A. Minato, and K. Suzuki Tetrahedron 38 1982 3347
49. K. Tamao, A. Minato, N. Miyake, T. Matsuda, Y. Kiso, and M. Kumada Chem. Lett. 1975 133
50. K. Tamao, K. Sumitani, Y. Kiso, M. Zembayashi, A. Fujioka, S. Kodama, I. Nakajima, A. Minato, and M. Kumada Bull. Chem. Soc. Jpn. 49 1976 1958
51. M. Kumada, K. Tamao, and K. Sumitani Org. Synth. 58 1978 127
52. M. Kumada Pure Appl. Chem. 52 1980 669
53. E. Wenkert, E.L. Michelotti, and C.S. Swindell J. Am. Chem. Soc. 101 1979 2246
54. E. Wenkert, E.L. Michelotti, C.S. Swindell, and M. Tingoli J. Org. Chem. 49 1984 4894
55. L.N. Pridgen J. Org. Chem. 47 1982 4319
56. A. Minato, K. Tamao, K. Suzuki, and M. Kumada Tetrahedron Lett. 21 1980 4017
57. J.W. Dankwardt Angew. Chem., Int. Ed. Engl. 43 2004 2428
58. W.A. Herrmann, V.P.W. Böhm, and C.-P. Reisinger J. Organomet. Chem. 576 1999 23
59. J. Huang, and S.P. Nolan J. Am. Chem. Soc. 121 1999 9889
60. The presence of terphenyl in the reaction mixture could be explained by the coupling of a second equivalent of Grignard on the methoxy substituent of 4-choroanisole.
61. A. Altomare, M.C. Burla, M. Camalli, G.L. Cascarano, C. Giacovazzo, A. Guagliardi, A.G.G. Moliterni, G. Polidori, and R. Spagn J. Appl. Cryst. 32 1999 115
62. G.M. Sheldrick, University of Göttingen, 1997.
63. L.J. Farrugia J. Appl. Cryst. 30 1997 565