Synthesis and structure of dinuclear silver(I) and palladium(II) complexes of 2,7-Bis(methylene)naphthalene-bridged bis-N-heterocyclic carbene ligands

Organometallics

Volumn 30, Issue 6, 2011, Pages 1366-1373

  Saito, Shinichi ^a   Saika, Mitsuya ^a   Yamasaki, Ryu ^a   Azumaya, Isao ^b   Masu, Hyuma ^b  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AG COMPLEX; CATALYTIC ACTIVITY; DIMETHYLNAPHTHALENE; DINUCLEAR; HIGH YIELD; MIZOROKI-HECK REACTION; MONODENTATES; N-HETEROCYCLIC CARBENE LIGANDS; NHC LIGANDS; PALLADIUM COMPLEXES; PD COMPLEX; SILVER COMPLEXES; X-RAY CRYSTALLOGRAPHIC ANALYSIS;

CARBON INORGANIC COMPOUNDS; CATALYST ACTIVITY; CHELATION; LIGANDS; NAPHTHALENE; ORGANIC COMPOUNDS; SILVER; SILVER COMPOUNDS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

PALLADIUM COMPOUNDS;

EID: 79952971559     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om1008583     Document Type: Article

References (69)

1. Reviews: Poyatos, M.; Mata, J. A.; Peris, E. Chem. Rev. 2009, 109, 3677-3707
2. Lin, J. C. Y.; Huang, R. T. W.; Lee, C. S.; Bhattacharyya, A.; Hwang, W. S.; Lin, I. J. B. Chem. Rev. 2009, 109, 3561-3598
3. Lin, I. J. B.; Vasam, C. S. Coord. Chem. Rev. 2007, 251, 642-670
4. Garrison, J. C.; Youngs, W. J. Chem. Rev. 2005, 105, 3978-4008
5. Lin, I. J. B.; Vasam, C. S. Comments Inorg. Chem. 2004, 25, 75-129
6. Polly, L. A. Heteroat. Chem. 2002, 13, 534-539
7. Wang, J.-W.; Li, Q.-S.; Xu, F.-B.; Song, H.-B.; Zhang, Z.-Z. Eur. J. Org. Chem. 2006, 2006, 1310-1316
8. Wan, X.-J.; Xu, F.-B.; Li, Q.-S.; Song, H.-B.; Zhang, Z.-Z. Inorg. Chem. Commun. 2005, 8, 1053-1055
9. Perry, M. C.; Cui, X.; Burgess, K. Tetrahedron: Asymmetry 2002, 13, 1969-1972
10. Nielsen, D. J.; Cavell, K. J.; Skelton, B. W.; White, A. H. Inorg. Chim. Acta 2006, 359, 1855-1869
11. Simons, R. S.; Custer, P.; Tessier, C. A.; Youngs, W. J. Organometallics 2003, 22, 1979-1982
12. Bonnet, L. G.; Douthwaite, R. E.; Hodgson, R. Organometallics 2003, 22, 4384-4386
13. Douthwaite, R. E.; Houghton, J.; Kariuki, B. M. Chem. Commun. 2004, 698-699
14. Nielsen, D. J.; Cavell, K. J.; Skelton, B. W.; White, A. H. Inorg. Chim. Acta 2002, 327, 116-125
15. Chen, W.; Wu, B.; Matsumoto, K. J. Organomet. Chem. 2002, 654, 233-236
16. For polymeric 2:1 complexes, see: Edworthy, I. S.; Rodden, M.; Mungur, S. A.; Davis, K. M.; Blake, A. J.; Wilson, C.; Schröder, M.; Arnold, P. L. J. Organomet. Chem. 2005, 690, 5710-5719
17. Melaiye, A.; Simons, R. S.; Milsted, A.; Pingitore, F.; Wesdemiotis, C.; Tessier, C. A.; Youngs, W. J. J. Med. Chem. 2004, 47, 973-977
18. Recent examples: Brown, D. H.; Nealon, G. L.; Simpson, P. V.; Skelton, B. W.; Wang, Z. Organometallics 2009, 28, 1965-1968
19. Liu, A.; Zhang, X.; Chen, W. Organometallics 2009, 28, 4868-4871
20. Baker, M.; Brown, D.; Haque, R.; Skelton, B.; White, A. J. Incl. Phenom. Macrocycl. Chem. 2009, 65, 97-109
21. Willans, C. E.; Anderson, K. M.; Paterson, M. J.; Junk, P. C.; Barbour, L. J.; Steed, J. W. Eur. J. Inorg. Chem. 2009, 2009, 2835-2843
22. Pugh, D.; Boyle, A.; Danopoulos, A. A. Dalton Trans. 2008, 1087-1094
23. Jean-Baptiste dit Dominique, F.; Gornitzka, H.; Hemmert, C. J. Organomet. Chem. 2008, 693, 579-583
24. Liu, A.; Zhang, X.; Chen, W.; Qiu, H. Inorg. Chem. Commun. 2008, 11, 1128-1131
25. Papini, G.; Bandoli, G.; Dolmella, A.; Lobbia, G. G.; Pellei, M.; Santini, C. Inorg. Chem. Commun. 2008, 11, 1103-1106
26. Nielsen, D. J.; Cavell, K. J.; Skelton, B. W.; White, A. H. Organometallics 2006, 25, 4850-4856
27. Wang, D.-Q. Acta Crystallogr. E 2006, 62, m1565-m1566
28. Wang, J.-W.; Song, H.-B.; Li, Q.-S.; Xu, F.-B.; Zhang, Z.-Z. Inorg. Chim. Acta 2005, 358, 3653-3658
29. Qin, D.; Zeng, X.; Li, Q.; Xu, F.; Song, H.; Zhang, Z.-Z. Chem. Commun. 2007, 147-149
30. Wan, X. J.; Xu, F. B.; Li, Q. S.; Song, H. B.; Zhang, Z. Z. Organometallics 2005, 24, 6066-6068
31. Nielsen, D. J.; Cavell, K. J.; Viciu, M. S.; Nolan, S. P.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 2005, 690, 6133-6142
32. For polymeric 2:2 complexes, see: Chiu, P. L.; Chen, C. Y.; Zeng, J. Y.; Lu, C. Y.; Lee, H. M. J. Organomet. Chem. 2005, 690, 1682-1687
33. Lee, K. M.; Wang, H. M. J.; Lin, I. J. B. J. Chem. Soc., Dalton Trans. 2002, 2852-2856
34. For tripodal NHC complexes, see: Wang, D.; Zhang, B.; He, C.; Wu, P.; Duan, C. Chem. Commun. 2010, 46, 4728-4730
35. Hu, X.; Tang, Y.; Gantzel, P.; Meyer, K. Organometallics 2003, 22, 612-614
36. Hahn, F. E.; Radloff, C.; Pape, T.; Hepp, A. Chem.-Eur. J. 2008, 14, 10900-10904
37. Melaiye, A.; Sun, Z.; Hindi, K.; Milsted, A.; Ely, D.; Reneker, D. H.; Tessier, C. A.; Youngs, W. J. J. Am. Chem. Soc. 2005, 127, 2285-2291
38. Baker, M. V.; Brown, D. H.; Haque, R. A.; Skelton, B. W.; White, A. H. Dalton Trans. 2004, 3756-3764
39. Reviews: Díez-González, S.; Marion, N.; Nolan, S. P. Chem. Rev. 2009, 109, 3612-3676
40. Organ, M. G.; Chass, G. A.; Fang, D.-C.; Hopkinson, A. C.; Valente, C. Synthesis 2008, 2008, 2776-2797
41. Normand, A. T.; Cavell, K. J. Eur. J. Inorg. Chem. 2008, 2008, 2781-2800
42. Hahn, F. E.; Jahnke, M. C. Angew. Chem., Int. Ed. 2008, 47, 3122-3172
43. Würtz, S.; Glorius, F. Acc. Chem. Res. 2008, 41, 1523-1533
44. Marion, N.; Nolan, S. P. Acc. Chem. Res. 2008, 41, 1440-1449
45. Kantchev, E. A. B.; O'Brien, C. J.; Organ, M. G. Angew. Chem., Int. Ed. 2007, 46, 2768-2813
46. Díez-González, S.; Nolan, S. Top. Organomet. Chem. 2007, 21, 47-82
47. Kantchev, E. A. B.; O'Brien, C. J.; Organ, M. G. Aldrichim. Acta 2006, 39, 97-111
48. Peris, E.; Crabtree, R. H. Coord. Chem. Rev. 2004, 248, 2239-2246
49. Crudden, C. M.; Allen, D. P. Coord. Chem. Rev. 2004, 248, 2247-2273
50. Herrmann, W. A.; Öfele, K.; v. Preysing, D.; Schneider, S. K. J. Organomet. Chem. 2003, 687, 229-248
51. Hillier, A. C.; Grasa, G. A.; Viciu, M. S.; Lee, H. M.; Yang, C.; Nolan, S. P. J. Organomet. Chem. 2002, 653, 69-82
52. Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290-1309
53. 2 complexes, see: Houghton, J.; Dyson, G.; Douthwaite, R. E.; Whitwood, A. C.; Kariuki, B. M. Dalton Trans. 2007, 3065-3073, and ref 5d
54. Makino, T.; Masu, H.; Katagiri, K.; Yamasaki, R.; Azumaya, I.; Saito, S. Eur. J. Inorg. Chem. 2008, 4861-4865
55. Saito, S.; Yamaguchi, H.; Muto, H.; Makino, T. Tetrahedron Lett. 2007, 48, 7498-7501
56. For a previous study that reported the synthesis of naphthalene-bridged bis-NHC ligands, see: Wong, W. W. H.; Phipps, D. E.; Beer, P. D. Polyhedron 2004, 23, 2821-2829
57. Terfort, A.; Görls, H.; Brunner, H. Synthesis 1997, 1997, 79-86
58. Tulloch, A. A. D.; Danopoulos, A. A.; Winston, S.; Kleinhenz, S.; Eastham, G. J. Chem. Soc., Dalton Trans. 2000, 4499-4506
59. Danopoulos, A. A.; Tulloch, A. A. D.; Winston, S.; Eastham, G.; Hursthouse, M. B. Dalton Trans. 2003, 1009-1015
60. Wang, H. M. J.; Lin, I. J. B. Organometallics 1998, 17, 972-975
61. Busetto, L.; Cristina Cassani, M.; Femoni, C.; Macchioni, A.; Mazzoni, R.; Zuccaccia, D. J. Organomet. Chem. 2008, 693, 2579-2591
62. Baker, M. V.; Brown, D. H.; Haque, R. A.; Skelton, B. W.; White, A. H. Dalton Trans. 2004, 3756-3764
63. Chen, W.; Liu, F. J. Organomet. Chem. 2003, 673, 5-12
64. Helgesson, G.; Jagner, S. J. Chem. Soc., Dalton Trans. 1990, 2413-2420
65. Yu, X.-Y.; Patrick, B. O.; James, B. R. Organometallics 2006, 25, 2359-2363
66. The dihedral angle is defined as the angle between the two planes, which are defined through three atoms of the imidazolin-2-ylidene ring (N, C(carbene), N).
67. An excess of NaI was added to convert the palladium complexes with a mixture of halogen atoms to the palladium iodide complex.
68. Campeau, L. C.; Thansandote, P.; Fagnou, K. Org. Lett. 2005, 7, 1857-1860
69. Pytkowicz, J.; Roland, S.; Mangeney, P.; Meyer, G.; Jutand, A. J. Organomet. Chem. 2003, 678, 166-179