Dinuclear cycloaurated complexes containing bridging (2-diphenylphosphino)phenylphosphine and (2-diethylphosphino)phenylphosphine, C6H4PR2 (R = Ph, Et). Carbon-carbon bond formation by reductive elimination at a gold(II)-gold(II) center

Journal of the American Chemical Society

Volumn 118, Issue 43, 1996, Pages 10469-10478

  Bennett, Martin A ^a   Bhargava, Suresh K ^a,b   Hockless, David C R ^a   Welling, Lee L ^a   Willis, Anthony C ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^b RMIT UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

GOLD DERIVATIVE; METAL COMPLEX;

ARTICLE; COMPLEX FORMATION; CRYSTALLOGRAPHY; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0029822967     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961511h     Document Type: Article

References (71)

1. Puddephatt, R. J. The Chemistry of Gold; Elsevier: Amsterdam. 1978; pp 61 and 116.
2. Puddephatt, R. J. In Comprehensive Coordination Chemistry; Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon: Oxford, 1987; Vol. 5, p 861.
3. Schmidbaur, H. Organogold Compounds, Gmelin Handbuch der Anorganischen Chemie; Springer: Berlin, 1980: pp 257-264.
4. Hall, K. P.; Mingos, D. M. P. Prog. Inorg. Chem. 1984, 32, 237.
5. Grohmann, A.; Schmidbaur, H. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 3, p 1.
6. Schmidbaur, H.; Franke, R. Inorg. Chim. Acta 1975, 13, 85.
7. Schmidbaur, H.; Mandl, J. R.; Frank, R.; Huttner, G. Chem. Ber. 1976, 109, 466.
8. Schmidbaur, H.; Wohlleben, A.; Wagner, F. G.; Van de Vondel, D.; Van der Kelen, G. Chem. Ber. 1977, 110, 2758.
9. Schmidbaur, H.; Wagner, E.; Wohlleben-Hammer, A. Chem. Ber. 1979, 112, 496.
10. Calabro, D. C.; Harrison, B. A.; Palmer, G. T.; Moguel, M. K.; Rebbert, R. L.; Burmeister, J. L. Inorg. Chem. 1981, 20, 4311.
11. Fackler, J. P., Jr.; Basil, J. D. Organometallics 1982, 1, 871.
12. Schmidbaur, H.; Jandik, P. Inorg. Chim. Acta 1983, 74, 97.
13. Fackler, J. P., Jr.; Basil, J. D. ACS Symp. Ser. 1983, 211, 201.
14. Mazany, A. M.; Fackler, J. P., Jr. J. Am. Chem. Soc. 1984, 106, 801.
15. Basil, J. D.; Murray, H. H.; Fackler, J. P., Jr.; Tocher, J.; Mazany, A. M.; Trczinska-Bancroft, B.; Knachel, H.; Dudis, D.; Delord, T. J.; Marler, D. O. J. Am. Chem. Soc. 1985, 107, 6908.
16. Fackler, J. P., Jr.; Trczinska-Bancroft, B. Organometallics 1985,4, 1891.
17. Dudis, D. S.; Fackler, J. P., Jr. Inorg. Chem. 1985, 24, 3758.
18. Murray, H. H., III; Porter, L. C.; Fackler, J. P., Jr.; Raptis, R. G. J. Chem. Soc., Dalton Trans. 1988, 2669.
19. Raptis, R. G.; Fackler, J. P., Jr.; Murray, H. H.; Porter, L. C. J. Am. Chem. Soc. 1989, 28, 4057.
20. Raptis, R. G.; Porter, L. C.; Emrich, R. J.; Murray, H. H.; Fackler, J. P., Jr. Inorg. Chem. 1990, 29, 4408.
21. Raptis, R. G.; Fackler, J. P., Jr.; Basil, J. D.; Dudis, D. S. Inorg. Chem. 1991, 30, 3072.
22. Raptis, R. G.; Murray, H. H.; Staples, R. J.; Porter, L. C.; Fackler, J. P., Jr. Inorg. Chem. 1993, 32, 5576.
23. Abicht, H-P.; Issleib, K. J. Organomet. Chem. 1978, 149, 209.
24. Papasergio, R.; Raston, C. L.; White, A. H. J. Chem. Soc., Dalton Trans. 1987, 3085.
25. Bennett, M. A.; Bhargava; S. K.; Griffiths, K. D.; Robertson, G. B.; Wickramasinghe, W. A.; Willis, A. C. Angew. Chem., Int. Ed. Engl. 1987, 26, 258.
26. Bennett, M. A.; Bhargava, S. K.; Griffiths, K. D.; Robertson, G. B. Angew. Chem., Int. Ed. Engl. 1987, 26, 260.
27. Bennett, M. A.; Milner, D. L. J. Am. Chem. Soc. 1969, 91, 6983.
28. Cole-Hamilton, D. J.; Wilkinson, G. J. Chem. Soc., Dalton Trans. 1977, 797.
29. Arnold, D. P.; Bennett, M. A.; Bilton, M. S.; Robertson, G. B. J. Chem. Soc., Chem. Commun. 1982, 115.
30. Inoguchi, Y.; Milewski-Mahrla, B.; Schmidbaur, H. Chem. Ber. 1982, 115, 3085.
31. Takeda, M.; Takahashi, M.; Ito, Y.; Takano, T.; Bennett, M. A.; Bhargava, S. K. Chem. Lett. 1990, 543.
32. Porter, L. C.; Fackler, J. P.; Jr. Acta Crystallogr., Sect. C 1986, 42, 1128.
33. Usón, R.; Laguna, A.; Laguna, M.; Jiménez, J.; Jones, P. G. J. Chem. Soc., Dalton Trans. 1991, 1361.
34. Nakamoto, K. Infrared and Raman Spectra of Inorganic and Coordination Compounds. 3rd ed.; Wiley-Interscience: New York, 1978; p 232.
35. Reference 35, p 244.
36. Siebert, H. Anwendungen der Schwingungsspektroskopie in der Anorganischen Chemie; Springer: Berlin, 1966; p 148.
37. Clark, R. J. H.; Tocher, J. H.; Fackler, J. P., Jr.; Neira, R.; Murray, H. H.; Knackel, H. J. Organomet. Chem. 1986, 303, 437.
38. Bardají, M.; Connelly, N. G.; Gimeno, M. C.; Jiménez, J.; Jones, P. G.; Laguna, A.; Laguna, M. J. Chem. Soc., Dalton Trans. 1994, 1163.
39. Bardají, M.; Gimeno, M. C.; Jones, P. G.; Laguna, A.; Laguna, M. Organometallics 1994, 13, 3415.
40. Bardají, M.; Jones, P. G.; Laguna, A.; Laguna, M. Organometallics 1995, 14, 1310.
41. Fackler, J. P., Jr.; Murray, H. H.; Basil, J. D. Organometallics 1984, 3, 821.
42. Allen, D. W.; Mann, F. G.; Millar, I. T. J. Chem. Soc. C 1967, 1869.
43. Miyamoto, T. K.; Matsuura, Y.; Okude, K.; Ichida, H.; Sasaki, Y. J. Organomet. Chem. 1989, 373, C8.
44. Desponds, A.; Schlosser, M. J. Organomet. Chem. 1996, 507, 257.
45. In contrast, axially dissymmetric bis(phosphines) containing additional ortho substituents, such as (6,6′-dimethylbiphenyl-2,2′-diyl)bis-(diphenylphosphine), can be made from the appropriate lithium reagent and Ph2PCl: Schmid, R.; Cereghetti, M.; Heiser, B.; Schönholzer, P.; Hansen, H-J. Helv. Chim. Acta 1988, 71, 897.
46. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry: Part A, Structure and Mechanism, 3rd ed.; Plenum: New York, 1990; p 235.
47. Garrou, P. E. Chem. Rev. 1981, 81, 229.
48. Bennett, M. A.; Berry, D. E.; Bhargava, S. K.; Ditzel, E. J.; Robertson, G. B.; Willis, A. C. J. Chem. Soc., Chem. Commun. 1987, 1613.
49. Kochi, J. K. Organometallic Mechanisms and Catalysis; Academic: New York, 1978; pp 532-542.
50. Halpern, J. Angew. Chem., Int. Ed Engl. 1985, 24, 274.
51. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry, 2nd ed.; University Science Books: Mill Valley, CA, 1987; pp 434-443.
52. Schmidbaur, H.; Hartmann, C.; Riede, J.: Huber, B.; Müller, G. Organometallics 1986, 5, 1652.
53. Trinquier, G.; Hoffmann, R. Organometallics 1984, 3, 370.
54. Reference 52, pp 333-353.
55. - (i-MNT = 1,1-dicyanoethylene-2,2-dithiolate), are promoted by coordinating solvents and by added halide ion: Khan, M. N. I.; Wang, S.; Fackler, J. P., Jr. Inorg. Chem. 1989, 28, 3579.
56. Tamaki, A.; Magennis, S. A.; Kochi, J. K. J. Am. Chem. Soc. 1974, 96, 6140.
57. Komiya, S.; Albright, T. A.; Hoffmann, R.; Kochi, J. K. J. Am. Chem. Soc. 1976, 98, 7255.
58. Bennett, M. A.; Welling, L. L.; Hockless, D. C. R. unpublished work; similar behavior is observed in the bis(ylide) series, see refs 7 and 12.
59. Talay, R.; Rehder, D. Z. Naturforsch. B 1981, 36, 459.
60. Lucas, H. J.; Kennedy, E. R. Organic Syntheses, Wiley: New York, 1955; Collect. Vol. III. p 482.
61. Coates, G. E.; Kowala, C.; Swan, J. M. Aust. J. Chem. 1966, 19, 539.
62. Tunney, S. E.; Stille, J. K. J. Org. Chem. 1987, 52, 748.
63. Hart, F. A. J. Chem. Soc. 1960, 3324.
64. Hartley, J. G.; Venanzi, L. M.; Goodall, D. C. J. Chem. Soc. 1963, 3930.
65. Harder, S.; Brandsma, L.; Kanters, J. A.; Duisenberg, A.; van Lenthe, J. J. Organomet. Chem. 1991, 420, 143.
66. IGOR PRO: Wave Metrics Inc., Lake Oswego, OR 97035, 1995.
67. Sheldrick, G. M. SHELXS-86. In Crystallographic Computing 3; Sheldrick, G. M., Krüger, C., Goddard, R., Eds.; Oxford University Press: Oxford, England, 1985; pp 175-189.
68. Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; Garcia-Gande, S.; Gould, R. O.; Smits, J. M. M.; Smykalla, C. PATTY: The DIRDIF Program System, Technical Report of The Crystallography Laboratory; University of Nijmegen, The Netherlands, 1992.
69. FOURR: Stewart, J.; Holden, J.; Doherty, R.: Hall, S. R. XTAL3.2 Reference Manual; Lamb: Perth, 1992.
70. Hall, S. R.; Flack, H. D.; Stewart, J. M., Eds. XTAL 3.2 Reference Manual. University of Western Australia, Geneva and Maryland. Lamb: Perth, 1992.
71. teXsan: Crystal Structure Analysis Package, Molecular Structure Corp., The Woodlands, TX 77381, 1985 and 1992.