Preparation and reactivities of PCP-type pincer complexes of nickel. Impact of different ligand skeletons and phosphine substituents

Organometallics

Volumn 27, Issue 21, 2008, Pages 5723-5732

  Castonguay, Annie ^a   Beauchamp, André L ^a   Zargarian, Davit ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTALLOGRAPHY; CYCLIC VOLTAMMETRY; LIGANDS; NICKEL ALLOYS; PHOSPHORUS COMPOUNDS; SINGLE CRYSTALS;

CATALYTIC PRECURSORS; CATALYTIC PROCESSES; COUPLING REACTIONS; DIPHOSPHINE LIGANDS; PHOSPHINE SUBSTITUENTS; PINCER COMPLEXES; TRANSMETALATION; VOLTAMMETRY MEASUREMENTS; X-RAY DIFFRACTIONS;

NICKEL;

EID: 56049095036     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om8005454     Document Type: Article

References (82)

1. For some of the original reports on PCP-type pincer complexes see: (a) Moulton, C. J.; Shaw, B. L. Dalton Trans. 1976, 1020.
2. (b) Al-Salem, N. A.; Empsall, H. D.; Markham, R.; Shaw, B. L.; Weeks, B. Dalton Trans. 1979, 1972.
3. (c) Al-Salem, N. A.; McDonald, W. S.; Markham, R.; Norton, M. C.; Shaw, B. L. Dalton Trans. 1980, 59.
4. (d) Crocker, C.; Errington, R. J.; Markham, R.; Moulton, C. J.; Odell, K. J.; Shaw, B. L. J. Am. Chem. Soc. 1980, 102, 4373.
5. (e) Crocker, C.; Errington, R. J.; Markham, R.; Moulton, C. J.; Shaw, B. L. Dalton Trans. 1982, 387.
6. (f) Crocker, C.; Empsall, H. D.; Errington, R. J.; Hyde, E. M.; McDonald, W. S.; Markham, R.; Norton, M. C.; Shaw, B. L.; Weeks, B. Dalton Trans. 1982, 1217.
7. (g) Briggs, J. R.; Constable, A. G.; McDonald, W. S.; Shaw, B. L. Dalton Trans. 1982, 1225.
8. (a) Albrecht, M.; van Koten, G. Angew. Chem., Int. Ed. 2001, 40, 3750.
9. (b) van der Boom, M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759.
10. Singleton, J. T. Tetrahedron 2003, 59, 1837.
11. (a) Sjövall, S.; Wendt, O. F.; Andersson, C. J. Chem. Soc., Dalton Trans. 2002, 1396.
12. (b) Ohff, M.; Ohff, A.; van der Boom, M. E.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687.
13. (c) Miyazaki, F; Yamaguchi, K.; Shibasaki, M. Tetrahedron Lett. 1999, 40, 7379.
14. (d) Naghipour, A.; Sabounchei, S. J.; Morales-Morales, D.; Canseco-González, D.; Jensen, C. M. Polyhedron 2007, 26, 1445.
15. (a) Gareau, D.; Sui-Seng, C.; Groux, L. F.; Brisse, F.; Zargarian, D. Organometallics 2005, 24, 4003.
16. (b) Chen, Y.; Sui-Seng, C.; Zargarian, D. Angew. Chem., Int. Ed. 2005, 44, 7721.
17. (c) Boucher, S.; Zargarian, D. Can. J. Chem. 2005, 84, 233.
18. (d) Chen, Y.; Sui-Seng, C.; Boucher, S.; Zargarian, D. Organometallics 2005, 24, 149.
19. (e) Fontaine, F.-G.; Zargarian, D. J. Am. Chem. Soc. 2004, 126, 8786.
20. (f) Groux, L. F.; Zargarian, D. Organometallics 2003, 22, 4759.
21. (g) Fontaine, F.-G.; Nguyen, R.-V.; Zargarian, D. Can. J. Chem. 2003, 81, 1299.
22. (h) Groux, L. F.; Zargarian, D. Organometallics 2003, 22, 3124.
23. (i) Groux, L. F.; Zargarian, D.; Simon, L. C.; Soares, J. B. P. J. Mol. Catal. A 2003, 19, 51.
24. (j) Rivera, E.; Wang, R.; Zhu, X. X.; Zargarian, D.; Giasson, R. J. Mol. Catal. A 2003, 325, 204-205.
25. (k) Zargarian, D. Coord. Chem. Rev. 2002, 157, 233-234.
26. (l) Wang, R.; Groux, L. F.; Zargarian, D. Organometallics 2002, 21, 5531.
27. (m) Wang, R.; Groux, L. F.; Zargarian, D. J. Organomet. Chem. 2002, 660, 98.
28. (n) Fontaine, F.-G.; Zargarian, D. Organometallics 2002, 21, 401.
29. (o) Dubois, M.-A.; Wang, R.; Zargarian, D.; Tian, J.; Vollmerhaus, R.; Li, Z.; Collins, S. Organometallics 2001, 20, 663.
30. (p) Groux, L. F.; Zargarian, D. Organometallics 2001, 20, 3811.
31. (q) Groux, L. F.; Zargarian, D. Organometallics 2001, 20, 3811.
32. (r) Fontaine, F.-G.; Dubois, M.-A.; Zargarian, D. Organometallics 2001, 20, 5156.
33. (s) Wang, R.; Bélanger-Gariépy, F.; Zargarian, D. Organometallics 1999, 18, 5548.
34. (t) Fontaine, F.-G.; Kadkhodazadeh, T.; Zargarian, D. Chem. Commun. 1998, 1253.
35. (u) Vollmerhaus, R.; Bélanger-Gariépy, F.; Zargarian, D. Organometallics 1997, 16, 4762.
36. (v) Huber, T. A.; Bayrakdarian, M.; Dion, S.; Dubuc, I.; Bélanger-Gariépy, F.; Zargarian, D. Organometallics 1997, 16, 5811.
37. (w) Bayrakdarian, M.; Davis, M. J.; Reber, C.; Zargarian, D. Can. J. Chem. 1996, 74, 2194.
38. (x) Huber, T. A.; Bélanger-Gariépy, F.; Zargarian, D. Organometallics 1995, 14, 4997.
39. For examples of PCP complexes of nickel see ref. 1a and:(a) Kennedy, A. R.; Cross, R. J.; Muir, K. W. Inorg. Chim. Acta 1995, 231, 195.
40. (b) Huck, W. T. S.; Snellink-Ruël, B.; van Veggel, F. C. J. M.; Reinhoudt, D. N. Organometallics 1997, 16, 4287.
41. (c) Bachechi, F. Struct. Chem. 2003, 14, 263.
42. (d) Kozhanov, K. A.; Bubnov, M. P.; Cherkasov, V. K.; Fukin, G. K.; Abakumov, G. A. Chem. Commun. 2003, 2610.
43. (e) Cámpora, J.; Palma, P.; del Río, D.; Álvarez, E. Organometallics 2004, 23, 1652.
44. (f) Cámpora, J.; Palma, P.; del Río, D.; Conejo, M. M.; Álvarez, E. Organometallics 2004, 23, 5653.
45. (g) van der Boom, M. E.; Liou, S. Y.; Shimon, L. J. W.; Ben-David, Y.; Milstein, D. Inorg. Chim. Acta 2004, 357, 4015.
46. Groux, L. F.; Bélanger-Gariépy, F.; Zargarian, D. Can. J. Chem. 2005, 83, 634.
47. Castonguay, A.; Sui-Seng, C.; Zargarian, D.; Beauchamp, A. L. Organometallics 2006, 25, 02.
48. Sui-Seng, C.; Castonguay, A.; Chen, Y.; Gareau, D.; Groux, L. F.; Zargarian, D. Top. Catal. 2006, 37, 81.
49. (a) Pandarus, V.; Zargarian, D. Chem. Commun. 2007, 978.
50. (b) Pandarus, V.; Zargarian, D. Organometallics 2007, 26, 4321.
51. Seligson, A. L.; Trogler, W. C. Organometallics 1993, 12, 738.
52. 4, the Cl analogue of 1, have been reported recently. Castonguay, A.; Beauchamp, A. L.; Zargarian, D. Acta Crystallogr. 2007, E63, m196.
53. Cambridge Structural Database search (Version 5.28 with updates up to November 2006): Allen, F. H. Acta Crystallogr. 2002, B58, 380.
54. Cámpora, J.; Palma, P.; del Río, D.; Álvarez, E. Organometallics 2004, 23, 1652.
55. z hybrid orbital and the symmetry-related MO on the Ph moiety.
56. sp bond distance in 5 to the mean of all the Ni-alkynyl bond lengths reported in the literature.
57. 1H) NMR spectroscopy.
58. Tamao, K.; Sumitani, K; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4374.
59. Corriu, R. J. P.; Masse, J. P. Chem. Commun. 1972, 144.
60. (a) Wang, Z.-X.; Wang, L. Chem. Commun. 2007, 2423.
61. (b) Liang, L.-C.; Chien, P.-S.; Lin, J.-M.; Huang, M.-H.; Huang, Y.-L.; Liao, J.-H. Organometallics 2006, 25, 1399.
62. 6): 70.5.
63. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Application of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987.
64. 31P signal for 4 as the only signal during the course of the catalysis and in the final reaction mixture suggests that the only P-bearing species involved in the coupling reaction are (PCP)NiX (X = Cl, Me).
65. ̇ radicals, is often proposed for the observation of homocoupling products. See for instance: Tsou, T. T.; Kochi, J. K. J. Am. Chem. Soc. 1979, 101, 7547.
66. 1/2 (complex 2) ∼170 mV.
67. sp3P ligand should not be suited to stabilizing an unpaired electron, but this alternative explanation cannot be ruled out.
68. III.
69. The corresponding value for the second independent molecule of the asymmetric unit was found to be 0.331 Å.
70. The τ parameter is calculated according to the relationship τ = (β-α)/60, wherein α and β refer to the largest basal angles in the complex (β > α); values approaching zero imply small degrees of deviation from an ideal square-pyramidal geometry, whereas values approaching 1 signal significant distortions toward a trigonal bipyramidal geometry: Addison, A. W.; Rao, T. N.; Reedijk, J.; van Rijn, J.; Verschoor, G. C. J. Chem. Soc., Dalton Trans. 1984, 1349.
71. For omer examples of Ni-alkyl complexes diat are resistant to β-H elimination see:(a) Liang, L.-C.; Lin, J.-M.; Hung, C.-H. Organometallics 2003, 22, 3007.
72. (b) Stollenz, M.; Rudolph, M.; Görls, H.; Walther, D. J. Organomet. Chem. 2003, 657, 153.
73. Geier, S.; Goddard, R.; Holle, S; Jolly, P. W.; Krüger, C.; Lutz, F. Organometallics 1997, 16, 1612.
74. The yield of ligand remains unchanged whether the synthesis is done under an argon or nitrogen atmosphere.
75. Rybtchinski, B.; Ben-David, Y.; Milstein, D. Organometallics 1997, 16, 3786.
76. SAINT Release 6.06, Integration Software for Single Crystal Data; Broker AXS Inc.: Madison, WI, 1999.
77. Sheldrick, G. M. SADABS, Bruker Area Detector Absorption Corrections; Bruker AXS Inc.: Madison, WI, 1999.
78. XPREP Release 5.10, X-ray data Preparation and Reciprocal Space Exploration Program; Broker AXS Inc.: Madison, WI, 1997.
79. SHELXTL Release 5.10, The Complete Software Package for Single Crystal Structure Determination; Bruker AXS Inc.: Madison, WI, 1997.
80. (a) Sheldrick, G. M. SHELXS97, Program for the Solution of Crystal Structures; Univ. of Gottingen: Germany, 1997.
81. (b) Sheldrick, G. M. SHELXL97, Program for the Refinement of Crystal Structures; University of Gottingen: Germany, 1997.
82. Spek, A. L. PLATON, Molecular Geometry Program; University of Utrecht: Holland, 2002.