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Volumn 127, Issue 12, 2005, Pages 4120-4121

The role of chelating diamine ligands in the Goldberg reaction: A kinetic study on the copper-catalyzed amidation of aryl iodides

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; DIAMINE; IODINE DERIVATIVE; LIGAND;

EID: 16244411305     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja050120c     Document Type: Article
Times cited : (260)

References (29)
  • 1
    • 0345329013 scopus 로고
    • For reviews, see: (a) Lindley, J. Tetrahedron 1984, 40, 1433.
    • (1984) Tetrahedron , vol.40 , pp. 1433
    • Lindley, J.1
  • 10
    • 37049061223 scopus 로고
    • For examples where increasing the [ligand] inhibits copper-promoted reactions, see: (a) Bacon, R. G. R.; Hill, H. A. O. J. Chem. Soc. 1964, 1097.
    • (1964) J. Chem. Soc. , pp. 1097
    • Bacon, R.G.R.1    Hill, H.A.O.2
  • 15
    • 16244422422 scopus 로고    scopus 로고
    • note
    • One explanation for the activity of catalysts based on 1,2-diamines is that they increase the oxidation potential of copper(I), thus facilitating the activation of the aryl halide; see ref 4b.
  • 21
    • 16244384277 scopus 로고    scopus 로고
    • note
    • 4 may limit the reaction rate due to mass transfer effects. However, using different stirring rates resulted in identical reaction rate profiles, thus ruling out the possibility of a mass transfer limited process.
  • 23
    • 16244409349 scopus 로고    scopus 로고
    • note
    • See Supporting Information.
  • 24
    • 16244405967 scopus 로고    scopus 로고
    • note
    • T, and [Amide] simplify eq 2 to the form: rate = a[3]/(1 + b[3]), where a and b are adjustable parameters.
  • 25
    • 16244377820 scopus 로고    scopus 로고
    • note
    • Reaction rate is independent of [base] at both low and high [3]. This is presumably due to saturation of the base in a nonpolar solvent, and thus, the [base] is treated as a constant. See Supporting Information for more details.
  • 29
    • 16244391200 scopus 로고    scopus 로고
    • note
    • Arylation of 5 in the absence of 3 did not proceed at temperatures between 0 °C and 90 °C.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.