Mechanism of the palladium-catalyzed metal-carbon bond formation. Isolation of oxidative addition and transmetalation intermediates

Organometallics

Volumn 15, Issue 24, 1996, Pages 5220-5230

  Cianfriglia, Paola ^a   Narducci, Valentina ^a   Lo Sterzo, Claudio ^a   Viola, Egidio ^a   Bocelli, Gabriele ^b   Kodenkandath, Thomas A ^b  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b Ctro Stud per Strutturistica D   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001520938     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9601965     Document Type: Article

References (67)

1. (a) Heck, R. F. Palladium in Organic Synthesis; Academic Press: New York, 1985.
2. (b) Stille, J. K. Pure Appl. Chem. 1985, 56, 1771.
3. (c) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
4. (d) Farina, V.; Krishnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434.
5. (e) Schlosser, M., Ed. Organometallics in Synthesis; John Wiley & Sons Ltd.: Chichester, England, 1994.
6. (f) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1987.
7. (g) Saa', J. M.; Martorell, G.; Garcia-Raso, A. J. Org. Chem. 1992, 57, 678.
8. (h) Mitchell, T. N. Synthesis 1992, 803.
9. (a) Lo Sterzo, C. J. Chem. Soc., Dalton Trans. 1992, 1989.
10. (b) Crescenzi, R. Tesi di Laurea, Università di Roma "La Sapienza", Roma, Italy, 1992.
11. (a) Crescenzi, R.; Lo Sterzo, C. Organometallics 1992, 11, 4301 and references therein,
12. (b) Viola, E.; Lo Sterzo, C.; Crescenzi, R.; Frachey, G. J. Organomet. Chem. 1995, 493, 55.
13. (c) Viola, E.; Lo Sterzo, C.; Crescenzi, R.; Frachey, G. J. Organomet. Chem. 1995, 493, C9.
14. (d) Trezzi, F.; Viola, E.; Lo Sterzo, C. Organometallics, in press.
15. (a) Bruce D. W.; O'Hare D. Inorganic Materials; John Wiley & Sons: Chichester, England, 1992.
16. (b) Sun, Y.; Taylor, N. J.; Carty, A. J. Organometallics 1992, 11, 4293.
17. (c) Lichtenberger, D. L.; Renshaw, S. K.; Wong, A.; Tagge, C. Organometallics 1993, 12, 3522.
18. (d) Beck, W.; Niemer, B.; Wieser, M. Angew. Chem. Int. Ed. Engl. 1993, 32, 923.
19. (e) Lang, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 547.
20. Morita, D. K.; Stille, J. K.; Norton, J. R. J. Am. Chem. Soc. 1995, 117, 8576 and references therein.
21. Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworths & Co: London, England, 1987.
22. (a) Brown, J. M.; Cooley, N. A. Organometallics 1990, 9, 353.
23. (b) Amatore, C.; Jutand, A.; Suarez, A. J. Am. Chem. Soc. 1993, 115, 9531 and references therein.
24. (c) Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
25. (d) Stang, P. J.; Kowalski, M. H.; Schiavelli, M. D.; Longford, D. J. Am. Chem. Soc. 1989, 111, 3347.
26. Baker, K. V.; Brown, J. M.; Cooley, N. A.; Huges, G. D.; Taylor, R. J. J. Organomet. Chem. 1989, 370, 397.
27. (a) Bullock, R. M.; Casey, C. P. Acc. Chem. Res. 1987, 20, 167. Stille, J. K.; Smith, C.; Anderson, O. P.; Miller, M. M. Organometallics 1989, 8, 1040.
28. (a) Bullock, R. M.; Casey, C. P. Acc. Chem. Res. 1987, 20, 167. Stille, J. K.; Smith, C.; Anderson, O. P.; Miller, M. M. Organometallics 1989, 8, 1040.
29. (b) Brumas, B.; de Caro, D.; Dahan, F.; de Montauzon, D.; Poliblanc, R. Organometallics 1993, 12, 1503.
30. (c) Ladipo, F. T.; Anderson, G. K.; Rath, N. P. Organometallics, 1994, 13, 4741.
31. Spadoni, L.; Lo Sterzo, C.; Crescenzi, R.; Frachey, G. Organometallics 1995, 14, 3149.
32. -1.
33. Narducci, V.; Cianfriglia, P.; Lo Sterzo, C. Work in progress.
34. (a) Mathey, F.; Lampin, J. P. Tetrahedron 1975, 31, 2685.
35. (b) Casey, C. P.; Bullock, R. M.; Fultz, W. C.; Rheingold, A. L. Organometallics 1982, 1, 1591.
36. (a) Bender, R.; Braunstein, P.; Jud, J.-M.; Dusausoy, Y. Inorg. Chem. 1983, 22, 3394 and references therein.
37. (b) Howard, K. E.; Rauchfuss, T. B.; Wilson, S. R. Inorg. Chem. 1988, 27, 3561.
38. (c) Zhengzhi, Z.; Xukun, W.; Yujun, S.; Xinkan, Y.; Honggen, W. Gaodeng Xuexiao Huaxue Xuebao (Chem. J. Chin. Univ.) 1990, 11, 255.
39. (d) Engel, P. F.; Pfeffer, M.; Fischer, J.; Dedieu, A. J. Chem. Soc., Chem. Commun. 1991, 1274.
40. (e) Engel, P. F.; Pfeffer, M.; Fischer, J. Organometallics 1994, 13, 4751.
41. Hirschon, A. S.; Musker, W. K.; Olmstead, M. M.; Dallas, J. L. Inorg. Chem. 1981, 20, 1702.
42. Bailey, N. A.; Mason, R. J. Chem. Soc. A 1968, 2594.
43. Fair, J. P.; Olmstead, M. M.; Balch, A. L. Inorg. Chem. 1983, 22, 1229.
44. (a) Janiak, C.; Schumann, H. Adv. Organomet. Chem. 1991, 33, 291.
45. (b) Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1984, 106, 4261.
46. (c) Broadley, K.; Lane, G. A.; Connelly, N. G.; Geiger, W. E. J. Am. Chem. Soc. 1983, 105, 2486.
47. Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047.
48. Negishi, E.; Takahashi, T.; Baba, S.; Van Horn, D. E.; Okukado, N. J. Am. Chem. Soc. 1987, 109, 2393.
49. (a) Stang, P. J.; Kowalski, M. H. J. Am. Chem. Soc. 1989, 111, 3356.
50. (b) Portnoy, M.; Milstein, D. Organometallics 1993, 12, 1655.
51. Shriver, D. F., Dredzon, M. A. The Manipulation of Air-Sensitive Compounds, 2nd ed.; Wiley-Interscience: New York, 1986.
52. (a) Kugel, M. Liebigs Ann. Chem. 1898, 299, 50.
53. (b) Drake, N. L.; Adams, J. R., Jr. J. Am. Chem. Soc. 1939, 61, 1326.
54. Ukay, T.; Kawazawa, H.; Ishii, Y.; Bonnett, J. J.; Ibers, J. A. J. Organomet. Chem. 1974, 65, 253.
55. Tate, D. P.; Knipple, W. R.; Augl, J. M. Inorg. Chem. 1962, 1, 433
56. Coulson, D. R. Inorg. Synth. 1972, 13, 121.
57. Lorberth, J. J. Organomet. Chem. 1969, 16, 327.
58. Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627.
59. Jones, K.; Lappert, M. F. J. Chem. Soc. 1965, 1944.
60. Winkle, M. R.; Lansinger, J. M.; Ronald, R. C. J. Chem. Soc., Chem. Commun. 1980, 87.
61. Belletti, D. A new hardware and software system for controlling the Philips PW1100 single crystal diffractometer with a personal computer; Internal Report 1/94; Centro di Studio per la Strutturistica Diffrattometrica del C.N.R., Parma, Italy, 1994.
62. North, A. C. T.; Phillips, D. C.; Mattews, F. S. Acta Crystallogr. 1968, A24, 351.
63. Walker, N.; Stuart, D. Acta Crystallogr. 1983, A39, 158.
64. Gluzinski, P. XRAY, Set of programs for X-ray structural calculations; Polish Academy of Sciences, Warszawa, Poland, 1989.
65. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M. C.; Polidori, C.; Camalli, M. J. Appl. Crystallogr. 1994, 27, 435.
66. Sheldrick, G. M. SHELX93. Program for the Refinement of Crystal Structures; University of Göttingen, Germany, 1993.
67. Rizzoli, C.; Sangermano, V.; Calestani, G.; Andreetti, G. D. J. Appl. Crystallogr. 1987, 20, 436.