Reductive routes to dinuclear d10-d10 palladium(0) complexes and their redistribution equilibria in solution

Organometallics

Volumn 20, Issue 14, 2001, Pages 2959-2961

  Reid, Steven M ^a   Fink, Mark J ^a  

^a Tulane University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DINUCLEAR COMPLEXES; FORMYLATION;

AROMATIC COMPOUNDS; CHELATION; CHEMICAL BONDS; COMPLEXATION; DECHLORINATION; DIMERS; DISSOCIATION; MONOMERS; PALLADIUM COMPOUNDS; PHASE EQUILIBRIA; REDUCTION; SOLUTIONS;

ORGANOMETALLICS;

EID: 0035833275     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om010281z     Document Type: Article

References (59)

1. (a) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: San Diego, CA, 1985.
2. (b) Hegedus, L. S. In Organometallics in Synthesis; Schlosser, M., Ed.; Wiley: New York, 1994; pp 383-459.
3. (c) Herman, W. A. In Applied Homogeneous Catalysis with Organometallic Compounds. A Comprehensive Handbook in Two Volumes; Cornils, B., Hermann, W. A., Eds.; VCH: New York, 1996; Vol. 2, pp 712-732.
4. Aryl-amination reactions: (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
5. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
6. (c) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852.
7. (d) Stille couplings: Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1.
8. (a) Portnoy, M.; Milstein, D. Organometallics 1993, 12, 1665.
9. (b) Ben-David, Y.; Portnoy, M.; Milstein, D. J. Am. Chem. Soc. 1989, 111, 8742.
10. (c) Ben-David, Y.; Portnoy, M.; Milstein, D. J. Chem. Soc., Chem. Commun. 1989, 1816.
11. (d) Ben-David, Y.; Gozin, M.; Portnoy, M.; Milstein, D. J. Mol. Catal. 1992, 73, 173.
12. Fryzuk, M. D.; Clentsmith, G. K. B.; Rettig, S. J. Organometallics 1996, 15, 2083.
13. 2"; Amatore, C.; Jutand, A. Coord. Chem. Rev. 1998, 178-180, 511.
14. n complexes (n = 1-4): (a) Coulson, D. R. Inorg. Synth. 1972, 13, 121.
15. (b) Malatesta, L.; Angolette, M. J. Chem. Soc. 1957, 1186.
16. (c) Fischer, E. O.; Werner, H. Chem. Ber. 1962, 95, 703.
17. (d) Kuran, W.; Musco, A. J. Organomet. Chem. 1972, 40, C47.
18. (e) Kuran, W.; Musco, A. Inorg. Chim. Acta 1975, 12, 187.
19. (f) Mann, B. E.; Musco, A. J. Chem. Soc., Dalton Trans. 1975, 1673.
20. (g) Urata, H.; Suzuki, H.; Moro-oka, Y.; Ikawa, T. J. Organomet. Chem. 1989, 364, 235.
21. (h) Grushin, V.; Alper, H. Organometallics 1993, 12, 1890.
22. (i) Grushin, V.; Bensimon, C.; Alper, H. Organometallics 1995, 14, 3259.
23. n complexes (n = 1, 2): (a) Hartwig, J. F.; Paul, F. J. Am. Chem. Soc. 1995, 117, 5373.
24. (b) Paul, F.; Patt, J.; Hartwig, J. F. J. Am. Chem. Soc. 1994, 116, 5969.
25. (c) Paul, F.; Patt, J.; Hartwig, J. F. Organometallics 1995, 14, 3030.
26. (d) Hartwig, J. F. Synlett 1997, 329.
27. (e) Louie, J.; Paul, F.; Hartwig, J. F. Organometallics 1996, 15, 2794.
28. Other proposed monophosphine "L-M(0)" intermediates: (a) Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1.
29. (b) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald S. L. J. Org. Chem. 2000, 65, 1158.
30. (c) Krause, J.; Cestaric, G.; Haack, K. J.; Seevogel, K.; Storm, W.; Pórschke, K. R. J. Am. Chem. Soc. 1999, 121, 9807.
31. (a) Amatore, C.; Jutand, A. J. Organomet. Chem. 1999, 576, 254.
32. (b) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314.
33. Pan, Y.; Mague, J. T.; Fink, M. J. J. Am. Chem. Soc. 1993, 115, 3842.
34. (a) Schager, F.; Bonrath, W.; Pörschke, K. R.; Kessler, M.; Krüger, C.; Seevogel, K. Organometallics 1997, 16, 4276.
35. (b) Schager, F.; Haack, K. J.; Mynott, R.; Rufinska, A.; Pörschke, K. R. Organometallics 1998, 17, 807.
36. (c) Trebbe, R.; Goddard, R.; Rufinska, A.; Seevogel, K.; Pörschke, K. R. Organometallics 1999, 18, 2466.
37. Doehring, A.; Goddard, R.; Hopp, G.; Jolly, P. W.; Kokel, N.; Krueger, C. Inorg. Chim. Acta 1994, 222(1-2), 179.
38. Reid, S. M.; Mague, J. T.; Fink, M. J. J. Am. Chem. Soc. 2001, 123, 4081.
39. 2 to give dipalladium complexes is limited to cases where n = 1.
40. 2Pd
41. 2Pd (Coalter, N. L.; Concolino, T. E.; Streib, W. E.; Hughes, C. G.; Rheingold, A. L.; Zaleski, J. M. J. Am. Chem. Soc. 2000, 122, 3112).
42. Diversi, P.; Ingrosso, G.; Lucherini, A.; Lumini, T.; Marchetti, F.; Adovasio, V.; Nardelli, M. J. Chem. Soc., Dalton Trans. 1988, 133.
43. 2: C, 45.60; H, 8.75. Found: C, 45.57; H, 8.80.
44. 8 gave irreproducible and low yields of the products.
45. A preliminary X-ray crystallographic analysis of 2 has been performed and supports the dinuclear structure shown in eq 1. A successful refinement could not be obtained due to chemical disorder within the crystal.
46. Harvey, P. D.; Gray, H. B. J. Am. Chem. Soc. 1988, 110, 2145.
47. (a) Dedieu, A.; Hoffmann, R. J. Am. Chem. Soc. 1978, 100, 2074.
48. (b) Sakaki, S.; Ogawa, M.; Musashi, Y. J. Phys. Chem. 1995, 99, 17134.
49. Portnoy, M.; Milstein, D. Organometallics 1993, 12, 1655.
50. (a) Woo, T. K.; Pioda, G.; Rothlisberger, U.; Togni, A. Organometallics 2000, 19, 2144.
51. (b) Suginome, M.; Oike, H.; Shuff, P. H.; Ito, Y. Organometallics 1996, 15, 2170.
52. (c) Suginome, M.; Oike, H.; Park S.-S.; Ito, Y. Bull. Chem. Soc. Jpn. 1996, 69, 289.
53. (d) Suginome, M.; Kato, Y.; Takeda, N.; Oike, H.; Ito, Y. Organometallics 1998, 17, 495.
54. (e) Murakami, M.; Yoshida, T.; Ito, Y. Organometallics 1994, 13, 2900.
55. (f) Pan, Y.; Mague, J. T.; Fink, M. J. Organometallics 1992, 11, 3495.
56. 2: C, 53.55; H, 7.95. Found: C, 53.48; H, 8.20.
57. After subspectral analysis, starting data and the experimental spectrum for 5 were used for iterative, least-squares optimization of chemical shifts and coupling constants using the gNMR 4.1 software package (Budzelaar, P. H. M. Cherwell Scientific Limited, 1999).
58. (a) Balch, A. L.; Hunt, C. T.; Lee, C. L.; Olmstead, M. M.; Farr, J. P. J. Am. Chem. Soc. 1981, 103, 3764.
59. (b) Lee, C.-L.; Yang, Y.-P.; Rettig, S. J.; James, B. R.; Nelson, D. A.; Lilga, M. A. Organometallics 1986, 5, 2220.