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Volumn , Issue 1, 1999, Pages 45-48

The palladium catalysed Suzuki coupling of 2- and 4-chloropyridines

Author keywords

Biaryl; Chloropyridines; Palladium; Suzuki coupling

Indexed keywords

CHLORINE DERIVATIVE; PALLADIUM; PYRIDINE DERIVATIVE;

EID: 0032962816     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2533     Document Type: Article
Times cited : (108)

References (50)
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    • For a recent review on catalytic cross-coupling reactions in biaryl synthesis, see: Stanforth, S. P. Tetrahedron 1998, 54, 263. For a review on Suzuki coupling, see: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
    • (1998) Tetrahedron , vol.54 , pp. 263
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  • 15
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    • For a recent review on catalytic cross-coupling reactions in biaryl synthesis, see: Stanforth, S. P. Tetrahedron 1998, 54, 263. For a review on Suzuki coupling, see: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
    • (1995) Chem. Rev. , vol.95 , pp. 2457
    • Miyaura, N.1    Suzuki, A.2
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    • The low reactivity of aryl chlorides in cross-coupling reactions is generally ascribed to their reluctance to oxidatively add to Pd(0). For discussions, see: a) Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047.
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    • Reference 9
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    • note
    • 12b
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    • a) For a general discussion concerning the reactivity of aromatic heterocycles towards nucleophilic substitution at carbon, see: Joule, J. A.; Mills, K.; Smith, G. F. Heterocyclic Chemistry, 3rd ed.; Chapman & Hall: London, 1995; p. 24.
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  • 21
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    • c) For examples of coupling reactions of chloroquinolines, see: Ciufolini, M. A.; Mitchell, J. W.; Roschangar, F. Tetrahedron Lett. 1996, 37, 8281.; Dunn, S. H.; McKillop, A. J. Chem. Soc., Perkin Trans. 1 1993, 8, 879.; Ali, N. M.; McKillop, A.; Mitchell, M. B.; Rebelo, R. A.; Wallbank, P. J. Tetrahedron 1992, 37, 8117.
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    • c) For examples of coupling reactions of chloroquinolines, see: Ciufolini, M. A.; Mitchell, J. W.; Roschangar, F. Tetrahedron Lett. 1996, 37, 8281.; Dunn, S. H.; McKillop, A. J. Chem. Soc., Perkin Trans. 1 1993, 8, 879.; Ali, N. M.; McKillop, A.; Mitchell, M. B.; Rebelo, R. A.; Wallbank, P. J. Tetrahedron 1992, 37, 8117.
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  • 23
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    • c) For examples of coupling reactions of chloroquinolines, see: Ciufolini, M. A.; Mitchell, J. W.; Roschangar, F. Tetrahedron Lett. 1996, 37, 8281.; Dunn, S. H.; McKillop, A. J. Chem. Soc., Perkin Trans. 1 1993, 8, 879.; Ali, N. M.; McKillop, A.; Mitchell, M. B.; Rebelo, R. A.; Wallbank, P. J. Tetrahedron 1992, 37, 8117.
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  • 24
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    • d) For examples of coupling reactions of chloropurines, see: Gundersen, L.-L. Tetrahedron Lett. 1994, 35, 3155.
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    • note
    • 4. After evaporation of the solvent, the oily residue was purified by bulb-to-bulb distillation (110°C, 1 mbar) to afford 11.15 g of pure 2-phenyl-pyridine(81 %).
  • 43
    • 0344211348 scopus 로고    scopus 로고
    • note
    • 3 was subsequently added, the colour of the solution changed, indicating the formation of a palladium-phosphine complex.
  • 48
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    • note
    • 24b
  • 49
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    • and literature cited therein
    • Self coupling of arylboronic acids has been described when the cross coupling is very slow. It has been turned into a useful synthetic method for the preparation of symmetrical biaryls: see Moreno-Mañas, M.; Pérez, M.; Pleixats, R. J. Org. Chem. 1996, 61, 2346 and literature cited therein.
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    • Moreno-Mañas, M.1    Pérez, M.2    Pleixats, R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.