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Volumn 349, Issue 11-12, 2007, Pages 1906-1916

Nitrogen ligands in copper-catalyzed arylation of phenols: Structure/activity relationships and applications

Author keywords

Arylation; Catalysis; Copper; Nitrogen ligands; Nucleophiles

Indexed keywords


EID: 34548462479     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200600628     Document Type: Article
Times cited : (113)

References (40)
  • 3
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    • For applications of our copper-based catalytic systems, see: a
    • For applications of our copper-based catalytic systems, see: a) M. Taillefer, A. Ouali, B. Renard, J.-F. Spindler, Chem. Eur. J. 2006, 20, 5301-5313;
    • (2006) Chem. Eur. J , vol.20 , pp. 5301-5313
    • Taillefer, M.1    Ouali, A.2    Renard, B.3    Spindler, J.-F.4
  • 10
    • 34548453400 scopus 로고    scopus 로고
    • efficient iron/copper co-catalyzed arylation of nitrogen nucleophiles: M. Taillefer, N. Xia, A. Ouali, Angew. Chem. 2007, 119, 952-954.
    • h) efficient iron/copper co-catalyzed arylation of nitrogen nucleophiles: M. Taillefer, N. Xia, A. Ouali, Angew. Chem. 2007, 119, 952-954.
  • 12
    • 34548423921 scopus 로고    scopus 로고
    • Chem. Abstr. 2003, 139, 69290;
    • Chem. Abstr. 2003, 139, 69290;
  • 13
    • 34548461004 scopus 로고    scopus 로고
    • M. Taillefer, H.-J. Cristau, P. P. Cellier, J.-F. Spindler, World Patent WO 03/050885, 2003;
    • b) M. Taillefer, H.-J. Cristau, P. P. Cellier, J.-F. Spindler, World Patent WO 03/050885, 2003;
  • 15
    • 34548413482 scopus 로고    scopus 로고
    • Chem. Abstr. 2004, 140, 16744;
    • Chem. Abstr. 2004, 140, 16744;
  • 16
    • 34548459210 scopus 로고    scopus 로고
    • M. Taillefer, H.-J. Cristau, P. P. Cellier, J.-F. Spindler, A. Ouali, World Patent WO 03/101966, 2003;
    • d) M. Taillefer, H.-J. Cristau, P. P. Cellier, J.-F. Spindler, A. Ouali, World Patent WO 03/101966, 2003;
  • 17
    • 34548457966 scopus 로고    scopus 로고
    • M. Taillefer, H.-J. Cristau, P. P. Cellier, J.-F. Spindler, Patent priority number FR 03 10253, 2004;
    • e) M. Taillefer, H.-J. Cristau, P. P. Cellier, J.-F. Spindler, Patent priority number FR 03 10253, 2004;
  • 18
    • 34548443196 scopus 로고    scopus 로고
    • J.-F. Spindler, M. Taillefer, H.-J. Cristau, P. P. Cellier, A. Ouali, World Patent WO 2005023731, 2005.
    • f) J.-F. Spindler, M. Taillefer, H.-J. Cristau, P. P. Cellier, A. Ouali, World Patent WO 2005023731, 2005.
  • 30
    • 0037631809 scopus 로고    scopus 로고
    • 4,4′-Disubstituted-2,2′-bipyridines were synthesized according to procedures described in the literature : G. J. ten Brink, I. W. C. E. Arends, M. Hoogenraad, G. Verspui, R. Sheldon, Adv. Synth. Catal. 2003, 345, 497-505; only the 4,4′-dimethylbipyridine was purchased from Aldrich.
    • 4,4′-Disubstituted-2,2′-bipyridines were synthesized according to procedures described in the literature : G. J. ten Brink, I. W. C. E. Arends, M. Hoogenraad, G. Verspui, R. Sheldon, Adv. Synth. Catal. 2003, 345, 497-505; only the 4,4′-dimethylbipyridine was purchased from Aldrich.
  • 31
    • 34548450084 scopus 로고    scopus 로고
    • The electro-donating ability of the substituents can be evaluated by Hammet σ coefficients (Table 2).
    • The electro-donating ability of the substituents can be evaluated by Hammet σ coefficients (Table 2).
  • 37
    • 34548408039 scopus 로고    scopus 로고
    • The reaction conditions used are the same than those previously reported in the case of the tetradentate ligand l:[2b] CuI (10 mol, ligand 6a (10 mol, 2N/ Cu) instead of ligand 1 (5 mol, corresponding also to the presence of two potential bonding sites per copper atom 2N/Cu, inexpensive tripotassium phosphate as the base, acetonitrile, 80°C
    • [2b] CuI (10 mol%), ligand 6a (10 mol%, 2N/ Cu) instead of ligand 1 (5 mol %, corresponding also to the presence of two potential bonding sites per copper atom (2N/Cu)), inexpensive tripotassium phosphate as the base, acetonitrile, 80°C
  • 38
    • 34548401485 scopus 로고    scopus 로고
    • The fraras-diamine-cyclohexane is at least 10-time more expensive than the aniline (checked for Acros Organics, Aldrich and Fluka suppliers).
    • The fraras-diamine-cyclohexane is at least 10-time more expensive than the aniline (checked for Acros Organics, Aldrich and Fluka suppliers).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.