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Volumn 125, Issue 14, 2003, Pages 4212-4222

Mechanism of the Stille reaction catalyzed by palladium ligated to arsine ligand: PhPdl(AsPh3)(DMF) is the species reacting with vinylstannane in DMF

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; DIMERS; DISSOCIATION; ORGANOMETALLICS; OXIDATION; REACTION KINETICS; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

EID: 0037427269     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0204978     Document Type: Article
Times cited : (136)

References (36)
  • 5
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    • Recent advances in the Stille reaction
    • (b) Farina, V.; Roth, G. P. Recent Advances in the Stille Reaction In Adv. Metalorg. Chem. 1996, 5, 1-53.
    • (1996) Adv. Metalorg. Chem. , vol.5 , pp. 1-53
    • Farina, V.1    Roth, G.P.2
  • 8
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    • For the mechanism of Stille reactions from aryl triflates, see ref 3 and (a) Farina, V.; Krisnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434-5444. (b) Casado, A. L.; Espinet, P.; Gallego, A. J. Am. Chem. Soc. 2000, 122, 11 771-11 782. (c) Casado, A. L.; Espinet P.; Gallego, A. M.; Martinez-Ilarduya, J. M. J. Chem. Soc. Chem. Comm. 2001, 120, 339-340.
    • (1993) J. Org. Chem. , vol.58 , pp. 5434-5444
    • Farina, V.1    Krisnan, B.2    Marshall, D.R.3    Roth, G.P.4
  • 9
    • 0034614060 scopus 로고    scopus 로고
    • For the mechanism of Stille reactions from aryl triflates, see ref 3 and (a) Farina, V.; Krisnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434-5444. (b) Casado, A. L.; Espinet, P.; Gallego, A. J. Am. Chem. Soc. 2000, 122, 11 771-11 782. (c) Casado, A. L.; Espinet P.; Gallego, A. M.; Martinez-Ilarduya, J. M. J. Chem. Soc. Chem. Comm. 2001, 120, 339-340.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 11771-11782
    • Casado, A.L.1    Espinet, P.2    Gallego, A.3
  • 10
    • 0035925221 scopus 로고    scopus 로고
    • For the mechanism of Stille reactions from aryl triflates, see ref 3 and (a) Farina, V.; Krisnan, B.; Marshall, D. R.; Roth, G. P. J. Org. Chem. 1993, 58, 5434-5444. (b) Casado, A. L.; Espinet, P.; Gallego, A. J. Am. Chem. Soc. 2000, 122, 11 771-11 782. (c) Casado, A. L.; Espinet P.; Gallego, A. M.; Martinez-Ilarduya, J. M. J. Chem. Soc. Chem. Comm. 2001, 120, 339-340.
    • (2001) J. Chem. Soc. Chem. Comm. , vol.120 , pp. 339-340
    • Casado, A.L.1    Espinet, P.2    Gallego, A.M.3    Martinez-Ilarduya, J.M.4
  • 14
    • 0242516086 scopus 로고    scopus 로고
    • note
    • 2
  • 16
    • 0242516088 scopus 로고    scopus 로고
    • note
    • Some deviation from the linearity was observed (Figure 1b). This is due to a variation of the ligand concentration during the course of the reaction. The exact kinetic law is given in eq 14 in the discussion part with n = 2.
  • 18
    • 0242516087 scopus 로고    scopus 로고
    • note
    • -.
  • 21
    • 0242684723 scopus 로고    scopus 로고
    • note
    • 6
  • 22
    • 0242600813 scopus 로고    scopus 로고
    • note
    • 3.
  • 23
    • 0242600815 scopus 로고    scopus 로고
    • note
    • 3 (Figure 7c).
  • 25
    • 0242432608 scopus 로고    scopus 로고
    • note
    • 6
  • 29
    • 0242600814 scopus 로고    scopus 로고
    • note
    • 4 value determined from the measured k value.
  • 30
    • 0242516084 scopus 로고    scopus 로고
    • note
    • + complex,
  • 32
    • 0242432588 scopus 로고    scopus 로고
    • This suggestion was further clarified through a personal communication with Prof. P. Espinet (Poster at the ISCH 13 Meeting in Tarragona, Spain. 3-7 September 2002). Casares, J. A.; Espinet, P.; Salas, G. Chem. Eur. J. 2002, 8, 4844-4853.
    • (2002) Chem. Eur. J. , vol.8 , pp. 4844-4853
    • Casares, J.A.1    Espinet, P.2    Salas, G.3
  • 33
    • 0242516083 scopus 로고    scopus 로고
    • note
    • 2] in chloroform. However, because Stille reactions are never performed in chloroform, this investigation has not been undertaken.
  • 34
    • 0242684721 scopus 로고    scopus 로고
    • note
    • 3 in THF, via the investigation of the kinetics of the catalytic reaction.
  • 35
    • 0242684722 scopus 로고    scopus 로고
    • note
    • This is an application of the steady-state approximation for a reactive moiety involved in a fast equilibrium with a non reactive species.


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