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Volumn 21, Issue 8, 2002, Pages 1537-1539

Nickel-catalyzed silaboration of small-ring vinylcycloalkanes: Regio- and stereoselective (E)-allylsilane formation via C-C bond cleavage

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; AROMATIC HYDROCARBONS; CATALYSTS; CHEMICAL BONDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SILANES; SUBSTITUTION REACTIONS; TRANSITION METALS;

EID: 0037820386     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om020007k     Document Type: Article
Times cited : (55)

References (28)
  • 8
    • 0000347750 scopus 로고
    • For noncatalyzed reactions of silylboranes, see: (a) Buynak, J. D. Geng, B. Organometallics 1995, 14, 3112.
    • (1995) Organometallics , vol.14 , pp. 3112
    • Buynak, J.D.1    Geng, B.2
  • 19
    • 0038024887 scopus 로고    scopus 로고
    • note
    • 2Ph resulted in lower yields (trace-10%) of 3a than that in the absence of the phosphine ligands.
  • 20
    • 0037686918 scopus 로고    scopus 로고
    • VCPs 2d and 2e were used as mixtures of E and Z isomers. E/Z ratios: 76/24 for 2d; 7/93 for 2e
    • VCPs 2d and 2e were used as mixtures of E and Z isomers. E/Z ratios: 76/24 for 2d; 7/93 for 2e.
  • 21
    • 0001373505 scopus 로고
    • Trost, B. M., Fleming, I., Paquette, L. A., Eds. Pergamon: Oxford
    • Hudlicky, T. Reed, J. W. In Comprehensive Organic Synthesis, Trost, B. M., Fleming, I., Paquette, L. A., Eds. Pergamon: Oxford, 1991; Vol. 5, p 899.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 899
    • Hudlicky, T.1    Reed, J.W.2
  • 23
    • 0038701238 scopus 로고    scopus 로고
    • note
    • Besides 2a(>95%), VCPs 2b (>95%), c (<5%), f (40%), g (50%), and h (90%) underwent the nickel-catalyzed isomerization under the same reaction conditions. The values in parentheses indicate the conversion of the VCPs after 8 h at 90 °C. As for reactions of VCPs 2d and 2e, products were not identifiable due to the low conversion. In these reactions, cis isomers were more rapidly consumed than the corresponding trans isomers.
  • 26
    • 0000512722 scopus 로고
    • For palladium-mediated reactions of vinylcyclobutanes, see: Larock, R. C. Varaprath, S. J. Org, Chem. 1984, 49, 3435. Larock, R. C. Yum, E. K. Tetrahedron 1996, 52, 2743.
    • (1984) J. Org, Chem. , vol.49 , pp. 3435
    • Larock, R.C.1    Varaprath, S.2
  • 27
    • 0343371814 scopus 로고    scopus 로고
    • For palladium-mediated reactions of vinylcyclobutanes, see: Larock, R. C. Varaprath, S. J. Org, Chem. 1984, 49, 3435. Larock, R. C. Yum, E. K. Tetrahedron 1996, 52, 2743.
    • (1996) Tetrahedron , vol.52 , pp. 2743
    • Larock, R.C.1    Yum, E.K.2
  • 28
    • 0034674966 scopus 로고    scopus 로고
    • For rhodium-catalyzed intramolecular [6 + 2] cycloadditions of 2-vinylcyclobutan-1-ones to alkenes, see: Wender, P. A. Correa, A. G. Sato, Y. Sun, R. J. Am. Chem. Soc. 2000, 122, 7815.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 7815
    • Wender, P.A.1    Correa, A.G.2    Sato, Y.3    Sun, R.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.