N-heterocyclic carbene functionalized group 7-9 transition metal phosphinidene complexes

Organometallics

Volumn 28, Issue 17, 2009, Pages 5166-5172

  Aktas, Halil ^a   Slootweg, J Chris ^a   Ehlers, Andreas W ^a   Lutz, Martin ^b   Spek, Anthony L ^b   Lammertsma, Koop ^a  

^a VU UNIVERSITY AMSTERDAM   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ANCILLARY LIGANDS; BACK-DONATION; BOND ENERGIES; CARBENES; CHARGED LIGANDS; CYCLOPENTADIENYLS; DEHYDROHALOGENATION; FUNCTIONALIZED; N-HETEROCYCLIC CARBENES; NET CHARGES; NHC LIGANDS; ORBITAL INTERACTION; PERIODIC TABLE; PHOSPHINIDENES; PHOSPHORUS ATOM; PRIMARY PHOSPHINE;

BENZENE; CHEMICAL BONDS; COMPLEXATION; DENSITY FUNCTIONAL THEORY; ELECTRONIC PROPERTIES; OSMIUM; PERIODIC STRUCTURES; PH EFFECTS; PHOSPHORUS; PHOSPHORUS COMPOUNDS; RHODIUM; TRANSITION METALS;

LIGANDS;

EID: 69949118375     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om900496y     Document Type: Article

References (73)

1. (a) Slootweg, J. C. Lammertsma, K. In science of Synthesis; Trost, B. M., Mathey, R., Eds.; Georg Thieme Verlag: Stuttgart, Germany, 2009; Vol. 42, pp 15-36.
2. (b) Mathey, F. Dalton Trans. 2007, 1861-1868.
3. (c) Lammertsma,K Top. Curr. Chem. 2003, 229, 95-119.
4. (d) Lammertsma, K.; Vlaar, M. J. M. Eur. J. Org. Chem. 2002, 1127-1138.
5. (e) Mathey, F.; Tran Huy, N. T.; Marinetti, A. Helv. Chim. Acta 2001, 84, 2938-2957.
6. (f) Stephan, D. W Angew. Chem. 2000, 112, 322-338;
7. Angew. Chem., Int. Ed. 2000, 39, 314-329.
8. (g) Cowley, A. H. Acc. Chem. Res. 1997, 30, 445-451.
9. Ehlers, A. W.; Baerends, E. J.; Lammertsma, K. J. Am. Chem. Soc. 2002, 124, 2831-2838.
10. (a) Termaten, A. T.; Schakel, M.; Ehlers, A. W.; Lutz, M.; Spek, A. L.; Lammertsma, K. Chem. Eur. J. 2003, 9, 3577-3582.
11. (b) Cummins, C. C.; Schrock, R R.; Davis, W M. Angew. Chem. 1993, 105, 758-761;
12. Angew. Chem., Int. Ed. 1993, 32, 756-759.
13. (c) Hou, Z.; Stephan, D. W. J. Am. Chem. Soc. 1992, 114, 10088-10089.
14. Melenkivitz, R.; Mindiola, D. J.; Hillhouse, G. L. J. Am. Chem. Soc. 2002, 124, 3846-3847.
15. (a) Basuli, F.; Tomaszewski, J.; Huffman, J. C.; Mindiola, D. J. J. Am. Chem. Soc. 2003, 125, 10170-10171.
16. (b) Basuli, R.; Bailey, B. C.; Huffman, J. C.; Baik, M.-H.; Mindiola, D. J. J. Am. Chem. Soc. 2004, 126, 1924-1925.
17. (c) Zhao, G.; Basuli, R.; Kilgore, U. J.; Fan, H.; Aneetha, H.; Huffman, J. C.; Wu, G.; Mindiola, D. J., J. Am. Chem. Soc. 2006, 128, 13575-13585 and references therein.
18. Termaten, A. T.; Nijbacker, T.; Schakel, M.; Lutz, M.; Spek, A. L.; Lammertsma, K. Chem. Eur. J. 2003, 9, 2200-2208.
19. Termaten, A. T.; Aktas, H.; Schakel, M.; Ehlers, A. W.; Lutz, M.; Spek, A. L.; Lammertsma, K. Organometallics 2003, 22, 1827-1834.
20. Termaten, A. T.; Nijbacker, T.; Schakel, M.; Lutz, M.; Spek, A. L.; Lammertsma, K. Organometallics 2002, 21, 3196-3202.
21. (a) Breen, T. L.; Stephan, D. W. J. Am. Chem. Soc. 1995, 117, 11914-11921. For reviews on phosphaalkenes, see:
22. (b) Le Floch, P. Coord. Chem. Rev. 2006, 250, 627-681.
23. (c) Mathey, F. Angew. Chem. 2003, 115, 1616-1643;
24. Angew. Chem., Int. Ed. 2003, 42, 1578-1604.
25. (d) Weber, L. Eur. J. Inorg. Chem. 2000, 2425-2441.
26. (e) Yoshifuji, M. J. J. Chem. Soc., Dalton Trans. 1998, 3343-3349.
27. (f) Weber, L. Angew. Chem. 1996, 108, 292-310;
28. Angew. Chem., Int. Ed. Engl. 1996, 35, 271-288.
29. (g) Gaumont, A. C.; Denis, J. M. Chem. Rev. 1994, 94, 1413-1439.
30. (h) Mathey, R Acc. Chem. Res. 1992, 25, 90-96.
31. (i) Appel, R., Multiple Bonds and Low Coordination in Phosphorus Chemistry; Regitz, M., Scherer, O. J., Eds.; Georg Thieme Verlag: Stuttgart, Germany, 1990.
32. (a) Tsang, C-W.; Yam, M.; Gates, D. P. J. Am. Chem. Soc. 2003, 125, 1480-1481.
33. (b) Gates, D. P. Top. Curr. Chem. 2005, 250, 107-126.
34. (c) Noonan, K J. T.; Gates, D. P. Angew. Chem. 2006, 118, 7429-7432;
35. Angew. Chem., Int. Ed. 2006, 45, 7271-7274.
36. Ozawa, F.; Yoshifuji, M. Dalton Trans. 2006,4987-4995.
37. (a) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann,W. A. Angew. Chem. 1998, 110, 2631-2633;
38. Angew. Chem., Int. Ed. 1998, 37, 2490-2493.
39. (b) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247-2250.
40. (c) Huang, J.; Stevens, E. D.; Nolan, S. P.; Petersen, J. L. J. Am. Chem. Soc. 1999, 121, 2674-2678.
41. (d) Huang, J.; Schanz, H.-J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5375-5380.
42. (e) Bielawski, C. W.; Grubbs, R. H. Angew. Chem. 2000, 112, 3025-3028;
43. Angew. Chem., Int. Ed. 2000, 39, 2903-2906.
44. Grubbs, R. H. Angew. Chem. 2006, 118, 3845-3850;
45. Angew. Chem., Int. Ed. 2006, 45, 3760-3765.
46. Aktas, H.; Slootweg, J. C.; Schakel, M.; Ehlers, A. W.; Lutz, M.; Spek, A. L.; Lammertsma, K. J. Am. Chem. Soc. 2009, 131, 6666-6667.
47. Lappert, M. F. J. Organomet. Chem. 2005, 690, 5467-5473.
48. Mercs, L.; Labat, G.; Neels, A.; Ehlers, A.; Albrecht, M. Organometallics 2006, 25, 5648-5656.
49. (a) Boehme, C.; Frenking, G. Organometallics 1998, 17, 5801-5809.
50. (b) Diez-Gonzalez, S.; Nolan, S. P. Coord. Chem. Rev. 2007, 251, 874-883.
51. (c) Jacobsen, H.; Correa, A.; Poater, A.; Costabile, C.; Cavallo, L. Coord. Chem. Rev. 2009, 253, 687-703.
52. 31P) 736.8), which is formed by arene exchange with the solvent; for more details, see ref 14.
53. *)].
54. Frenking, G.; Antes, i; Boehme, M.; Dapprich, S.; Ehlers, A.; Jonas, V.; Neuhaus, A.; Otto, M.; Stegmann, R.; Veldkamp, A.; Vyboyshchikov, S. F. In Reviews in Computational Chemistry; Lipkowitz, K. B., Boyd, D. B., Eds.; VCH: New York, 1996; Vol. 8, p 63.
55. ADF2006.01; SCM, Theoretical Chemistry, Vrije Universiteit, Amsterdam, The Netherlands, http://www.scm.com/.
56. Vosko, S. H.; WiIk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200-1211.
57. Becke, A. D. Phys. Rev. A 1988, 38, 3098-3100.
58. Perdew, J. P. Phys. Rev. B 1986, 33, 8822-8824.
59. (a) Fan, L.; Versluis, L.; Ziegler, T.; Baerends, E. J.; Raveneck, W. Int. J. Quantum Chem., Quantum Chem. Symp. 1988, S22, 173-181.
60. (b) Versluis, L.; Ziegler, T. J. Chem. Phys. 1988, 88, 322-328.
61. van Lenthe, E.; Ehlers, A. W.; Baerends, E. J. J. Chem. Phys. 1999, 110, 8943-8953.
62. (a) Morokuma, K. Acc. Chem. Res. 1977, 10, 294-300.
63. (b) Ziegler, T.; Rauk, A. Inorg. Chem. 1979, 18, 1755-1759.
64. (c) Ziegler, T.; Rauk, A. Theor. Chim. Acta 1977, 46, 1-10.
65. Bennett, M. A.; Huang, T. N.; Matheson, T. W.; Smith, A. K. Inorg. Synth. 1982, 21, 74-78.
66. Kuhn, N.; Kratz, T. Synthesis 1993, 561-562.
67. Arduengo, A. J. III; Dias, H. V. R.; Harlov, R. L.; Kline, M. J. Am. Chem. Soc. 1992, 114, 5530-5534.
68. Cowley, A. H.; Kilduff, J. E.; Newman, T. H.; Pakulski, M. J. Am. Chem. Soc. 1982, 104, 5820-5821.
69. van den Winkel, Y.; Bastiaans, H. M. M.; Bickelhaupt, F. J. Organomet. Chem. 1991, 405, 183-194.
70. Duisenberg, A. J. M.; Kroon-Batenburg, L. M. J.; Schreurs, A. M. M. J. Appl. Crystallogr. 2003, 36, 220-229.
71. Sheldrick, G. M. SADABS: Area-Detector Absorption Correction, v2.10; Universität Göttingen, Göttingen, Germany, 1999.
72. Sheldrick, G. M. Acta Crystallogr. 2008, A64, 112-122.
73. Spek, A. L. J. Appl. Crystallogr. 2003, 36, 7-13.