Characterization and reactivity of the tetrametallic Pd2-Mo 2 complex Ph(Bu)P(η5-C5H 4)Mo(CO)3Pd(μ-I)2PdMo(CO) 3(η55-C5H4)P(Ph)Bu and its use to model Pd-catalyzed cross-coupling reactions leading to M-C≡C bonds

Organometallics

Volumn 23, Issue 17, 2004, Pages 4105-4111

  Angelucci, Francesco ^a   Ricci, Antonella ^a   Masi, Dante ^b   Bianchini, Claudio ^b   Lo Sterzo, Claudio ^c  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b Area di Ricerca CNR di Firenze   (Italy)

^c UNIVERSITY OF TERAMO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL BONDS; CHROMATOGRAPHIC ANALYSIS; COMPLEXATION; CRYSTAL ATOMIC STRUCTURE; CRYSTALS; DIFFUSION; INFORMATION ANALYSIS; INTERMETALLICS; OXIDATION; PALLADIUM COMPOUNDS; PHOSPHORUS COMPOUNDS; POLARIZATION; REACTION KINETICS; SPECTROSCOPIC ANALYSIS;

CATALYTIC PROCESS; CROSS COUPLING REACTIONS; LIGANDS; TRANSMETALATION;

ORGANOMETALLICS;

EID: 4344652937     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0400595     Document Type: Article

References (68)

1. Schlosser, M. Organometallics in Synthesis; John Wiley & Sons Ltd.: Chichester, England, 1994.
2. (b) Heck, R. F. Palladium in Organic Synthesis; Academic Press: New York, 1985.
3. (c) Tsuji, J. Palladium Reagents and Catalysts, Innovation in Organic Synthesis; John Wiley & Sons Ltd.: Chichester, England, 1996.
4. (d) Mitchell, T. N. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J. Eds.; Wiley-VCH: Weinheim, Germany, 1998.
5. (e) J. Organomet. Chem. 2002, 053 (issue 1-2), Special Issue, 30 Years of the Cross-Coupling Reaction.
6. Lo Sterzo, C. J. Chem. Soc., Dalton Trans. 1992, 1989.
7. (b) Lo Sterzo, C. Synlett 1999, 1704.
8. (c) Crescenzi, R.; Lo Sterzo, C. Organometallics 1992, 11, 4301.
9. (d) Viola, E.; Lo Sterzo C.; Crescenzi, R.; Frachey, G. J. Organomet. Chem. 1995, 493, 55.
10. (e) Viola, E.; Lo Sterzo C.; Crescenzi, R.; Frachey, G. J. Organomet. Chem. 1995, 495, C9.
11. Viola, E.; Lo Sterzo, C.; Trezzi, F. Organometallics 1996, 15, 4352.
12. (b) Buttinelli, A.; Viola, E.; Antonelli, E.; Lo Sterzo, C. Organometallics 1998, 17, 2574.
13. (c) Antonelli, E.; Rosi, P.; Lo Sterzo, C.; Viola, E. J. Organomet. Chem. 1999, 578, 210.
14. (d) Altamura, P.; Giardina, G.; Lo Sterzo, C.; Russo, M. V. Organometallics 2001, 20, 4360.
15. (e) La Groia, A.; Ricci, A.; Bassetti, M.; Masi, D.; Bianchini, C.; Lo Sterzo, C. J. Organomet. Chem. 2003, 683, 406.
16. Spadoni, L.; Lo Sterzo, C.; Crescenzi, R.; Frachey, G. Organometallics 1995, 14, 3149.
17. (b) Cianfriglia, P.; Narducci, V.; Lo Sterzo, C.; Viola, E.; Bocelli, G.; Kodenkandath, T. A. Organometallics 1996, 15, 5220.
18. (c) Tollis, S.; Narducci, V.; Cianfriglia, P.; Lo Sterzo, C.; Viola, E. Organometallics 1998, 17, 2388.
19. (d) Ricci, A.; Angelucci, F.; Bassetti, M.; Lo Sterzo, C. J. Am. Chem. Soc. 2002, 124, 1060.
20. (e) Ricci, A.; Lo Sterzo, C. J. Organomet. Chem. 2002, 653, 177.
21. (f) Angelucci, F.; Ricci, A.; Lo Sterzo, C.; Masi, D.; Bianchini, C.; Bocelli, G. Organometallics 2002, 21, 3001.
22. Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; John Wiley & Sons: New York, 1998.
23. (b) Gillie, A.; Stille, J. K. J. Am. Chem. Soc. 1980, 102, 4933.
24. (c) Tatsumi, K.; Hoffmann, R.; Yamamoto, A.; Stille, J. K. Bull. Chem. Soc. Jpn. 1981, 54, 1857.
25. (d) Stang, P. J.; Kowalski, M. H.; Schiavelli, M. D.; Longford, D. J. Am. Chem. Soc. 1989, 111, 3347.
26. (e) Brown, J. M.; Cooley, N. A. Organometallics 1990, 9, 353.
27. (f) Farina, V.; Krishnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434.
28. (g) Amatore, C.; Jutand, A.; Suarez, A. J. Am. Chem. Soc. 1998, 115, 9531, and references therein,
29. (h) Morita, D. K.; Stille, J. K.; Norton, J. R. J. Am. Chem. Soc. 1995, 117, 8576, and references therein,
30. Amatore, C.; Carré, E.; Jutand, A.; Tanaka, H.; Ren, Q.; Torii, S. Chem. Eur. J. 1996, 2, 957.
31. (j) Mateo, C.; Cárdenas, D. J.; Fernández-Rivas, C.; Echavarren, A. M. Chem. Eur. J. 1996, 2, 1596.
32. (k) Amatore, C.; Broeker, G.; Jutand, A.; Khalil, F. J. Am. Chem. Soc. 1997, 119, 5176.
33. (l) Louie, J.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 11598.
34. (m) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
35. Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
36. (b) Casado, A. L.; Espinet, P. J. Am. Chem. Soc. 1998, 120, 8978.
37. (c) Casado, A.; Espinet, P.; Gallego, A. M. J. Am. Chem. Soc. 2000, 122, 11771.
38. (d) Casado, A. L.; Espinet, P.; Gallego, A. M.; Martinez-Ilarduya, J. M. Chem. Commun. 2001, 339.
39. (e) Amatore, C.; Bucaille, A.; Fuxa, A.; Jutand, A.; Meyer, G.; Ndedi Ntepe, A. Chem. Eur. J. 2001, 2134.
40. (f) Casares, J. A.; Espinet, P.; Salas, G. Chem. Eur. J. 2002, 4844.
41. 8
42. Barbier, J. P.; Braunstein, P. J. Chem. Res (S) 1978, 412.
43. (b) Bender, R.; Braunstein, P.; Jud, J. M.; Dusausoy, Y. Inorg. Chem. 1983, 22, 3394, and references therein.
44. Butler, I. R.; Cullen, W. R.; Rettig, S. J. Organometallics 1987, 6, 872.
45. (b) Mathey, F.; Lampin, J. P. Tetrahedron 1975, 31, 2685.
46. (c) Deschamps, B.; Mathey, F. Phosphorus Sulfur 1983, 17, 317.
47. 3 (0.01 mL) was added to the solution to provide the lock signal. A prevalent signal at -27.2 ppm attributable to 14 is present in the spectrum.
48. Complex 14 was very sensitive and its isolation was hampered by the invariable formation of the corresponding phoshinoxide derivative. Evidently the absence of the stabilizing phenyl groups on Cp and the presence of the electron-donor butyl group on phosphorus have dramatically increased the sensitivity of complex 14 with respect to the similar, more stable compounds 1 and 2.
49. Arena, G. C.; Rotondo, E.; Faraone, F.; Lanfranchi, M.; Tiripicohio, A. Organometallics 1991, 10, 3874.
50. Wheatley, N.; Kalck, P. Chem. Rev. 1999, 99, 3379.
51. Thiele, G.; Brodersen, K.; Krause, E. Holle B. Chem. Ber. 1988, 101, 2771.
52. (b) Brunet, L.; Mercier, F.; Ricard, L.; Mathey, F. Angew. Chem., Int. Ed. Engl. 1994, 33, No. 7.
53. Mason, R.; Wheller, A. G. J. Chem. Soc. A 1968, 2549.
54. (b) Holden, J. R.; Baezinger, N. C. J. Am. Chem. Soc. 1955, 77, 4987.
55. (c) Clark, G. R.; Orbell, J. D. J. Organomet. Chem. 1981, 215, 121.
56. 31P NMR spectra of a chloroform solution of 15 containing increasing amounts of DMF, the pair of signals appearing at 46.7 and 47.2 ppm attributable to 15a and 15b, respectively, are progressively replaced by the signal at 49.8 attributable to 17.
57. Amatore, C.; Bahsoun, A. A.; Jutand, A.; Meyer, G.; Ndedi Ntepe, A.; Ricard, L. J. Am. Chem. Soc. 2003, 125, 4212.
58. 7 for lock purposes.
59. 4
60. 4a
61. 4e
62. 31P NMR spectroscopy the disappearance of signals of starting material is accompanied by the formation of a species displaying a group of four doublets of doublets signals, which, upon prolonged warming, remain the only species in solution.
63. To overcome reluctance of palladium to be extruded from 21, the reductive elimination process was also carried out by treating 21 (formed according to the procedure outlined in Scheme 4) in the presence of bis-1,2- diphenylphosphinoethane (dppe). However, instead of acting as scavenging agent for Pd, thus favoring formation of 22 (Scheme 5), dppe added to 21 caused the formation of 23, whose structure was assigned on the basis of spectroscopic data.
64. Tate, D. P.; Knipple, W. R.; Augl, J. M. Inorg. Chem. 1962, 1, 433.
65. Wilson, A. J. C. International Tables for X-Ray Crystallography; Kluwer Academic: Dordrecht, 1992; Vol. C, p 500.
66. (b) Wilson, A. J. C. International Tables for X-Ray Crystallography; Kluwer Academic: Dordrecht, 1992; Vol. C, p 219.
67. Sheldrick, G. M. SHELX97. Program for Crystal Structure Determination; University of Göttingen: Germany, 1997.
68. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G.; Giaco-vazzo, C.; Guagliardi, A.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 32, 115.