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Volumn 62, Issue 16, 1997, Pages 5242-5243

New monoorganostannanes as efficient reagents for palladium-Catalyzed coupling reactions

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EID: 0000350624     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo970465g     Document Type: Article
Times cited : (88)

References (35)
  • 3
    • 84858839656 scopus 로고
    • Pergamon Press: London Eds.
    • Abel, E. A., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: London, 1995; Vol. 12, pp 200-221.
    • (1995) , vol.12 , pp. 200-221
    • Abel, E.A.1    Stone, F.G.A.2    Wilkinson, G.3
  • 14
    • 58149324217 scopus 로고
    • 119Sn NMR spectrum by shielding the signal (δ = -129.1 ppm for 2a compared to -81.8 ppm for 2b and -84.6 ppm for 7). For similar phenomena observed on monoallyltrihalogenotins see also: Fouquet, E.; Gabriel, A.; Maillard, B.; Pereyre, M. Bull. Soc. ChIm. Fr. 1995, 132, 590.
    • (1995) Bull. Soc. ChIm. Fr. , vol.132 , pp. 590
    • Fouquet, E.1    Gabriel, A.2    Maillard, B.3    Pereyre, M.4
  • 18
    • 84858824332 scopus 로고    scopus 로고
    • v anion A, and the third equivalent is consumed for the halogen exchange of the tin-halogen bond created during the coupling
    • v anion A, and the third equivalent is consumed for the halogen exchange of the tin-halogen bond created during the coupling.
  • 28
    • 84858832458 scopus 로고    scopus 로고
    • Typical procedure: 1-Iodohexyne (1.85 mmol) was added to a solution of stannylene 1 (1.85 mmol) in THF (4 mL) and stirred for 30 min at rt. TBAF (5.9 mL, 1 M) was added, after concentration, dioxane (8 mL), iodobenzene (1.23 mmol), and tetrakis(triphenylphosphine)palladium (0.015 mmol) were added, and the reaction mixture was refluxed for 2 h. After cooling and removal of the solvent, purification on silica gel afforded 20 in 83% yield
    • Typical procedure: 1-Iodohexyne (1.85 mmol) was added to a solution of stannylene 1 (1.85 mmol) in THF (4 mL) and stirred for 30 min at rt. TBAF (5.9 mL, 1 M) was added, after concentration, dioxane (8 mL), iodobenzene (1.23 mmol), and tetrakis(triphenylphosphine)palladium (0.015 mmol) were added, and the reaction mixture was refluxed for 2 h. After cooling and removal of the solvent, purification on silica gel afforded 20 in 83% yield.


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