The mechanism of the Stille reaction investigated by electrospray ionization mass spectrometry

Journal of Organic Chemistry

Volumn 72, Issue 15, 2007, Pages 5809-5812

  Santos, Leonardo S ^a   Rosso, Giovanni B ^b   Pilli, Ronaldo A ^b   Eberlin, Marcos N ^b  

^a UNIVERSIDAD DE TALCA   (Chile)

^b UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; DRUG INFUSION; ELECTROSPRAY IONIZATION; MASS SPECTROMETRY; PALLADIUM; POSITIVE IONS;

CATALYTIC CYCLE; MOLECULAR ION; STILLE REACTION; TANDEM VERSION;

REACTION KINETICS;

PALLADIUM COMPLEX;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; ELECTROSPRAY MASS SPECTROMETRY; GAS; ONLINE MONITORING; STILLE REACTION; TANDEM MASS SPECTROMETRY;

EID: 34547093393     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062512n     Document Type: Article

References (48)

1. (a) Tsuji, J. Palladium Reagents and Catalysis: Innovations in Organic Chemistry; Wiley: New York, 1995.
2. (b) Milstein, D.; Stille, J. K. J. Am. Chem. Soc. 1978, 100, 3636.
3. (c) Farina, V.; Krishnamurthy, V.; Scott, W. J. The Stille Reaction; John Wiley & Sons, Inc.: New York, 1998.
4. (a) Espinet, P.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 4704.
5. (b) Stille, J. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
6. (c) Jutand, A. Eur. J. Inorg. Chem. 2003, 2017.
7. (d) Napolitano, E.; Farina, V.; Persico, M. Organometallics 2003, 22, 4030.
8. (a) Ricci, A.; Angelucci, F.; Bassetti, M.; Sterzo, C. L. J. Am. Chem. Soc. 2002, 124, 1060.
9. (b) Casado, A. L.; Espinet, P. J. Am. Chem. Soc. 1998, 120, 8978.
10. (c) Jutand, A.; Mosleh, A. Organometallics 1995, 14, 1810.
11. (d) Jutand, A.; Négri, S. Organometallics 2003, 22, 4229.
12. (e) Cárdenas, D. J.; Mateo, C.; Echavarren, A. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 2445.
13. (f) Casado, A. L.; Espinet, P. J. Am. Chem. Soc. 2000, 122, 11771. For a review see ref 4.
14. (a) Casado, A. L.; Espinet, P.; Gallego, A. M.; Martínez-Ilarduya, J. M. Chem. Commun. 2001, 339.
15. (b) Amatore, C.; Jutand, A. J. Organomet. Chem. 1999, 576, 254.
16. (c) Amatore, C.; Jutand, A. Acc. Chem. Res. 2000, 33, 314.
17. (d) Amatore, C.; Bahsoun, A. A.; Jutand, A.; Meyer, G.; Ntepe, A. N.; Ricard, L. J. Am. Chem. Soc. 2003, 125, 4212.
18. (a) Whitehouse, C. M.; Dreyer, R. N.; Yamashita, M.; Fenn, J. B. Anal. Chem. 1985, 57, 675.
19. (b) Cole, R. B. In Electrospray Ionization Mass Spectroscopy; John Wiley & Sons Inc.: New York, 1997.
20. (a) Santos, L. S.; Pavam, C. H.; Almeida, W. P.; Coelho, F.; Eberlin, M. N. Angew. Chem., Int. Ed. 2004, 43, 4330.
21. (b) Raminelli, C.; Prechtl, M. H. G.; Santos, L. S.; Eberlin, M. N.; Comasseto, J. V. Organometallics 2004, 23, 3990.
22. (c) Domingos, J. B.; Longhinotti, E.; Brandão, T. A. S.; Bunton, C. A.; Santos, L. S.; Eberlin, M. N.; Nome, F. J. Org. Chem. 2004, 69, 6024.
23. (d) Meyer, S.; Metzger, J. O. Anal. Bioanal. Chem. 2003, 377, 1108.
24. (e) Meyer, S.; Koch, R.; Metzger, J. O. Angew. Chem., Int. Ed. 2003, 42, 4700.
25. (f) Meurer, E. C.; Santos, L. S.; Pilli, R. A.; Eberlin, M. N. Org. Lett. 2003, 5, 1391.
26. (g) Griep-Raming, J.; Meyer, S.; Bruhn, T.; Metzger, J. O. Angew. Chem., Int. Ed. 2002, 41, 2738.
27. (h) Ferraz, H. M. C.; Gonçalo, E. R. S.; Pereira, F. L. C.; Santos, L. S.; Eberlin, M. N. J. Org. Chem. 2004, 70, 110.
28. (i) Domingos, J. B.; Longhinotti, E.; Brandão, T. A. S.; Bunton, C. A.; Santos, L. S.; Eberlin, M. N.; Nome, F. J. Org. Chem. 2004, 69, 7898.
29. (j) Sabino, A. A.; Machado, A.; Correa, C. R. D.; Eberlin, M. N. Angew. Chem., Int. Ed. 2004, 43, 2514.
30. (a) Hinderling, C.; Adlhart, C.; Chen, P. Angew. Chem., Int. Ed. 1998, 37, 2685.
31. (b) Chen, P. Angew. Chem., Int. Ed. 2003, 42, 2832.
32. (a) de la Mora, J. F.; Van Berckel, G. J.; Enke, C. G.; Cole, R. B.; Martinez-Sanchez, M.; Fenn, J. B. J. Mass Spectrom. 2000, 35, 939.
33. (b) Koch, K. J.; Gozzo, F. C.; Nanita, S. C.; Takats, Z.; Eberlin, M. N.; Cooks, R. G. Angew. Chem., Int. Ed. 2002, 41, 1721.
34. (c) Eberlin, M. N.; Gozzo, F. C.; Consorti, C. S.; Dupont, J. Chem. - Eur. J. 2004, 10, 6187.
35. (d) Neto, B. A. S.; Ebeling, G.; Gonçalves, R. S.; Gozzo, F. C.; Eberlin, M. N.; Dupont, J. Synthesis 2004, 8, 1155.
36. (e) DaSilveira Neto, B. A.; Santos, L. S.; Nachtigall, F. M.; Eberlin, M. N.; Dupont, J. Angew. Chem., Int. Ed. 2006, 45, 7521.
37. (a) Hartley, F. R. Organomet. Chem. Rev. A 1970, 6, 119.
38. (b) Rosevear, D. T.; Stone, F. G. A. J. Chem. Soc. A 1968, 164.
39. (c) Coulson, D. R. Inorg. Synth. 1972, 13, 121.
40. (d) Mann, B. E.; Musco, A. J. Chem. Soc., Dalton Trans. 1975, 1673.
41. (e) Fauvarque, J.-F.; Pflüger, F.; Troupel, M. J. Organomet. Chem. 1981, 208, 419.
42. (f) Amatore, C.; Pflüger, F. Organometallics 1990, 9, 2276.
43. Zenobi, R.; Knochenmuss, R. Mass Spectrom. Rev. 1998, 17, 337.
44. Tomazela, D. M.; Gozzo, F. C.; Eberling, G.; Dupont, J.; Eberlin, M. N. Inorg. Chim. Acta 2004, 357, 2349.
45. Eberlin, M. N. Mass Spectrom. Rev. 1997, 16, 113.
46. For a recent example, see: Qian, R.; Liao, Y. X.; Guo, Y. L.; Guo, H. J. Am. Soc. Mass Spectrom. 2006, 17, 1582.
47. (a) Santos, L. S.; Metzger, J. O. Angew. Chem., Int. Ed. 2006, 45, 977.
48. (b) Santos, L. S.; Knaack, L.; Metzger, J. O. Int. J. Mass Spectrom. 2005, 246, 84 and references therein.