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Volumn 40, Issue 9, 2011, Pages 910-912

Pd/C-catalyzed and water-mediated hiyama cross-coupling reaction using an electron-deficient phosphine ligand

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EID: 80052607197     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2011.910     Document Type: Article
Times cited : (18)

References (49)
  • 3
    • 80052598375 scopus 로고    scopus 로고
    • For reviews of Hiyama cross-coupling, see, ed. by E. Negishi, A. de Meijere, Wiley-Interscience, New York
    • For reviews of Hiyama cross-coupling, see: T. Hiyama, E. Shirakawa, in Handbook of Organopalladium Chemistry for Organic Synthesis, ed. by E. Negishi, A. de Meijere, Wiley-Interscience, New York, 2002, Vol. 1, pp. 285301
    • (2002) Handbook of Organopalladium Chemistry for Organic Synthesis , vol.1 , pp. 285301
    • Hiyama, T.1    Shirakawa, E.2
  • 15
    • 33846893890 scopus 로고    scopus 로고
    • For a review, see:
    • For a review, see: L. Yin, J. Liebscher, Chem. Rev. 2007, 107, 133.
    • (2007) Chem. Rev. , vol.107 , pp. 133
    • Yin, L.1    Liebscher, J.2
  • 21
    • 80052557006 scopus 로고    scopus 로고
    • Erratum:
    • G. Zhang, Synthesis 2005, 537; Erratum:
    • (2005) Synthesis , vol.537
    • Zhang, G.1
  • 23
    • 15444371592 scopus 로고    scopus 로고
    • Erratum:
    • G. Zhang, Synlett 2005, 619; Erratum:
    • (2005) Synlett , vol.619
    • Zhang, G.1
  • 32
    • 0037006237 scopus 로고    scopus 로고
    • Köhler et al. demonstrated the effect of the properties of the Pd/Cs, such as Pd particle size and surface area, on the reaction progress, see
    • Köhler et al. demonstrated the effect of the properties of the Pd/Cs, such as Pd particle size and surface area, on the reaction progress, see: K. Köhler, R. G. Heidenreich, J. G. E. Krauter, U. Pietsch, Chem.-Eur. J. 2002, 8, 622.
    • (2002) Chem.-Eur. J. , vol.8 , pp. 622
    • Köhler, K.1    Heidenreich, R.G.2    Krauter, J.G.E.3    Pietsch, U.4
  • 33
    • 70450181102 scopus 로고    scopus 로고
    • Buchwald reported that the electron-deficient nature of the ligand is important in facilitating the transmetallation during the palladiumcatalyzed N-arylation of secondary acyclic amides, see
    • Buchwald reported that the electron-deficient nature of the ligand is important in facilitating the transmetallation during the palladiumcatalyzed N-arylation of secondary acyclic amides, see: J. D. Hicks, A. M. Hyde, A. M. Cuezva, S. L. Buchwald, J. Am. Chem. Soc. 2009, 131, 16720.
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 16720
    • Hicks, J.D.1    Hyde, A.M.2    Cuezva, A.M.3    Buchwald, S.L.4
  • 37
    • 41849131493 scopus 로고    scopus 로고
    • Recently, a very low catalyst loading Hiyama cross-coupling reaction using oxime-derived palldacycles as catalysts in 50% NaOH solution was reported by C. Nájera et al. although only the homocoupled product derived from 4-bromoanisole was obtained using 0.5 mol% of Pd/C as a catalyst: see
    • Recently, a very low catalyst loading Hiyama cross-coupling reaction using oxime-derived palldacycles as catalysts in 50% NaOH solution was reported by C. Nájera et al. although only the homocoupled product derived from 4-bromoanisole was obtained using 0.5 mol% of Pd/C as a catalyst: see: E. Alacid, C. Nájera, J. Org. Chem. 2008, 73, 2315
    • (2008) J. Org. Chem. , vol.73 , pp. 2315
    • Alacid, E.1    Nájera, C.2
  • 39
    • 50149109621 scopus 로고    scopus 로고
    • The electron-deficient arylsilanes bearing an electron-withdrawing chloro group required a shorter time to complete the reaction, probably due to the enhanced electrophilicity of the silicon atoms facilitating the formation of the active silicate species for the facile transmetallation with palladium species (Table 2, Entries 3 vs. 2 and Entries 6 vs. 5), see
    • The electron-deficient arylsilanes bearing an electron-withdrawing chloro group required a shorter time to complete the reaction, probably due to the enhanced electrophilicity of the silicon atoms facilitating the formation of the active silicate species for the facile transmetallation with palladium species (Table 2, Entries 3 vs. 2 and Entries 6 vs. 5), see: K. H. Shukla, P. DeShong, J. Org. Chem. 2008, 73, 6283.
    • (2008) J. Org. Chem. , vol.73 , pp. 6283
    • Shukla, C.K.H.1    DeShong, P.2
  • 49
    • 80052598129 scopus 로고    scopus 로고
    • Supporting Information is available electronically on the CSJJournal Web site
    • Supporting Information is available electronically on the CSJJournal Web site, http://www.csj.jp/journals/chem-lett/index.html.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.