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Volumn 344, Issue 2, 2002, Pages 172-183

Oxime-Derived Palladium Complexes as Very Efficient Catalysts for the Heck-Mizoroki Reaction

Author keywords

C C coupling; Catalysts; Metallacycles; N ligands; Palladium

Indexed keywords


EID: 19044389954     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(200202)344:2<172::AID-ADSC172>3.0.CO;2-9     Document Type: Article
Times cited : (169)

References (75)
  • 43
    • 0034638745 scopus 로고    scopus 로고
    • [22]), the catalytic activity of benzaldoxime-and benzophenone oximepalladacycles in the Heck coupling reaction has been subjected to study: S. Iyer, C. Ramesh, Tetrahedron Lett. 2000, 41, 8981-8984.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 8981-8984
    • Iyer, S.1    Ramesh, C.2
  • 50
    • 0348205422 scopus 로고    scopus 로고
    • note
    • [8,11,12,17]).
  • 53
    • 0348205425 scopus 로고    scopus 로고
    • note
    • Phenyl triflate gave very poor yields (25% conversion with methyl acrylate and 0.25 mol % of 16d). Diazonium salts like 4-bromobenzenediazonium tetrafluoroborate afforded higher conversions but together with high yields of phenyl bromide under similar conditions.
  • 54
    • 0346944817 scopus 로고    scopus 로고
    • note
    • Commercially available solvents were used without further purification and no change in efficiencies or yields were detected when the reaction was carried out under nitrogen atmosphere.
  • 57
    • 0348205423 scopus 로고    scopus 로고
    • note
    • 3.
  • 59
    • 0346944818 scopus 로고    scopus 로고
    • note
    • One of the referees kindly suggested that the fact that the TOF becomes higher at lower catalyst loadings strongly suggests an equilibrium between monomeric Pd, which is the actual catalyst, with the palladium nanoparticles. At lower initial Pd concentrations this equilibrium will be shifted to the monomeric form, increasing the TOF.
  • 60
    • 0035959456 scopus 로고    scopus 로고
    • For very recent review about Heck chemistry of aryl bromides and chlorides, see: N. J. Whitcombe, K. K. M. Hii, S. E. Gibson, Tetrahedron 2001, 57, 7449-7476.
    • (2001) Tetrahedron , vol.57 , pp. 7449-7476
    • Whitcombe, N.J.1    Hii, K.K.M.2    Gibson, S.E.3
  • 62
    • 0030598098 scopus 로고    scopus 로고
    • b) T. Jeffery, Tetrahedron 1996, 52, 10113-10130.
    • (1996) Tetrahedron , vol.52 , pp. 10113-10130
    • Jeffery, T.1
  • 70
    • 0346944816 scopus 로고    scopus 로고
    • note
    • -1) and with a very low 22% yield. Better yield (69%) is obtained with higher catalyst loadings (TON = 690).
  • 74
    • 0001075641 scopus 로고    scopus 로고
    • For a review about annulation reactions, see: R. C. Larock, J. Organomet. Chem. 1999, 576, 111-124.
    • (1999) J. Organomet. Chem. , vol.576 , pp. 111-124
    • Larock, R.C.1
  • 75
    • 0348205421 scopus 로고    scopus 로고
    • note
    • [6c].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.