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Volumn 132, Issue 11, 2010, Pages 3674-3675

A highly efficient palladium/copper cocatalytic system for direct arylation of heteroarenes: An unexpected effect of Cu(xantphos)I

Author keywords

[No Author keywords available]

Indexed keywords

ARYLATIONS; CHEMICAL EQUATIONS; COCATALYST; HETEROARENES; HETEROCYCLES; LOW LOADING; MILD REACTION CONDITIONS; PALLADIUM CATALYST; XANTPHOS;

EID: 77949807476     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja100354j     Document Type: Article
Times cited : (307)

References (33)
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    • (a) Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998.
    • (1998) Metal-Catalyzed Cross-Coupling Reactions
  • 2
    • 84890973385 scopus 로고    scopus 로고
    • Ackermann, L., Ed.; Wiley-VCH: Weinheim, Germany
    • (b) Modern Arylation Methods; Ackermann, L., Ed.; Wiley-VCH: Weinheim, Germany; 2009.
    • (2009) Modern Arylation Methods
  • 22
    • 77949828962 scopus 로고    scopus 로고
    • A multikilogram process based on this system was run successfully.
    • A multikilogram process based on this system was run successfully.
  • 23
    • 0035901659 scopus 로고    scopus 로고
    • 2 are competent palladium catalyst partners.
    • 2 are competent palladium catalyst partners.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 1513
    • Li, G.Y.1
  • 24
    • 77949839088 scopus 로고    scopus 로고
    • 3CN.
    • 3CN.
  • 25
    • 77949842762 scopus 로고    scopus 로고
    • The coupling experiment using 0.25 mol % Pd and Xantphos in the absence of 1 gave <5% product.
    • The coupling experiment using 0.25 mol % Pd and Xantphos in the absence of 1 gave <5% product.
  • 26
    • 77949821356 scopus 로고    scopus 로고
    • IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene.
    • IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene.
  • 28
    • 50249118513 scopus 로고    scopus 로고
    • 1H NMR studies showed strong binding of 2 with the former to form the corresponding complex, but the analogous interaction was not observed with the latter. A similar explanation has been proposed in N-oxide C-H arylations. See: Gorelsky, S. L; Lapointe, D.; Fagnou, K. J. Am. Chem. 2008, 130, 10848.
    • (2008) J. Am. Chem. , Issue.130 , pp. 10848
    • Gorelsky, S.L.1    Lapointe, D.2    Fagnou, K.3
  • 29
    • 77949805346 scopus 로고    scopus 로고
    • D = 1.3) indicates that deprotonation is unlikely to be the rate-determining step.
    • D = 1.3) indicates that deprotonation is unlikely to be the rate-determining step.
  • 31
    • 33746929476 scopus 로고    scopus 로고
    • A similar mechanism was proposed in Pd/Cu-catalyzed decarboxylative coupling: Goossen, L. J.; Deng, G.; Levy, L. M. Science 2006, 313, 662.
    • (2006) Science , vol.313 , pp. 662
    • Goossen, L.J.1    Deng, G.2    Levy, L.M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.