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Volumn 121, Issue 41, 1999, Pages 9550-9561

Highly active palladium catalysts for Suzuki coupling reactions

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; BROMIDE; CHLORIDE; HALIDE; PALLADIUM;

EID: 0032747809     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992130h     Document Type: Article
Times cited : (1126)

References (68)
  • 1
    • 0344576287 scopus 로고    scopus 로고
    • Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, Chapter 2
    • Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; Chapter 2.
    • (1998) Metal-Catalyzed Cross-Coupling Reactions
    • Suzuki, A.1
  • 13
    • 0002442679 scopus 로고    scopus 로고
    • (c) Suzuki couplings of aryl chlorides catalyzed by palladium carbene complexes have been reported. See: Herrmann, W. A.; Reisinger, C.-P.; Spiegler, M. J. Organomet. Chem. 1998, 557, 93-96. Electron-rich aryl chlorides are effectively coupled if the proper carbene ligand is chosen. See: Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804- 3805.
    • (1998) J. Organomet. Chem. , vol.557 , pp. 93-96
    • Herrmann, W.A.1    Reisinger, C.-P.2    Spiegler, M.3
  • 14
    • 0033612378 scopus 로고    scopus 로고
    • (c) Suzuki couplings of aryl chlorides catalyzed by palladium carbene complexes have been reported. See: Herrmann, W. A.; Reisinger, C.-P.; Spiegler, M. J. Organomet. Chem. 1998, 557, 93-96. Electron-rich aryl chlorides are effectively coupled if the proper carbene ligand is chosen. See: Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804-3805.
    • (1999) J. Org. Chem. , vol.64 , pp. 3804-3805
    • Zhang, C.1    Huang, J.2    Trudell, M.L.3    Nolan, S.P.4
  • 22
    • 0345438376 scopus 로고    scopus 로고
    • note
    • 2 catalyst system has also been shown to be effective for room-temperature catalytic amination of aryl chlorides; see ref 9a.
  • 23
    • 0344144872 scopus 로고    scopus 로고
    • note
    • Ligands 2 and 4 are now commercially available from Strem Chemical Co.
  • 26
    • 0000631025 scopus 로고
    • Primary and secondary alkoxides are known to reduce aryl halides in the presence of palladium catalysts. Zask, A.; Helquist, P. J. Org. Chem. 1978, 43, 1619-1620.
    • (1978) J. Org. Chem. , vol.43 , pp. 1619-1620
    • Zask, A.1    Helquist, P.2
  • 35
    • 0345438374 scopus 로고    scopus 로고
    • note
    • No catalyst has been reported which is effective for Suzuki coupling reactions to form biaryls with four ortho substituents; to the best of our knowledge, only one isolated yield (12%) has been for the synthesis of a tetrasubstituted biaryl (using Suzuki coupling) has been reported. See ref 15c.
  • 37
    • 0003464638 scopus 로고    scopus 로고
    • Prentice Hall: Upper Saddle River, New Jersey
    • (a) It is well-known that the use of electron-rich phosphine ligands accelerates the rate of oxidative addition of aryl halides to Pd(0). See: Spessard, G. O.; Meissler, G. L. Organometallic Chemistry; Prentice Hall: Upper Saddle River, New Jersey, 1996; pp 171-175.
    • (1996) Organometallic Chemistry , pp. 171-175
    • Spessard, G.O.1    Meissler, G.L.2
  • 38
    • 33751386097 scopus 로고
    • 2 (dippp = 1,3-bis(diisopropylphosphino)propane) at 38 °C. Portnoy, M.; Milstein, D. Organometallics 1993, 12, 1665-1673.
    • (1993) Organometallics , vol.12 , pp. 1665-1673
    • Portnoy, M.1    Milstein, D.2
  • 47
    • 0001186913 scopus 로고
    • Pergamon Press: Oxford
    • Monophosphine palladium complexes have been demonstrated to be catalytically active intermediates in other palladium-catalyzed processes. Oxidative addition, transmetalation, and reductive elimination often proceed at higher rates if coordinatively unsaturated intermediates are accessible. See: (a) Farina, V. Comprehensive Organometallic Chemistry, 2nd ed.; Pergamon Press: Oxford, 1995; Vol. 12, pp 161-240.
    • (1995) Comprehensive Organometallic Chemistry, 2nd Ed. , vol.12 , pp. 161-240
    • Farina, V.1
  • 48
    • 1842740801 scopus 로고    scopus 로고
    • and references therein
    • (b) Hartwig, J. F. Synlett 1997, 329-340 and references therein.
    • (1997) Synlett , pp. 329-340
    • Hartwig, J.F.1
  • 49
    • 0344144869 scopus 로고    scopus 로고
    • note
    • A detailed mechanistic study on both Suzuki coupling and catalytic animation will be reported separately.
  • 50
    • 37049111384 scopus 로고
    • Biaryl-forming reductive elimination from Pt(II) has been postulated to occur via a transition state in which both arenes are perpendicular to the coordination plane. See: Braterman, P. S.; Cross, R. J.; Young, G. B. J. Chem. Soc., Dalton Trans. 1 1977, 1892-1897.
    • (1977) J. Chem. Soc., Dalton Trans. 1 , pp. 1892-1897
    • Braterman, P.S.1    Cross, R.J.2    Young, G.B.3
  • 52
    • 0002271959 scopus 로고
    • Schlosser, M., Ed.; John Wiley and Sons: West Sussex, England
    • Hegedus, L. S. In Organometallics in Synthesis; Schlosser, M., Ed.; John Wiley and Sons: West Sussex, England, 1994; p 448.
    • (1994) Organometallics in Synthesis , pp. 448
    • Hegedus, L.S.1
  • 54
    • 0345438372 scopus 로고    scopus 로고
    • note
    • Reactions in which argon purges were used instead of the evacuation/ backfill cycles (at all points required in the procedure) gave similar results.


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