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Volumn 349, Issue 17-18, 2007, Pages 2673-2676

Ligand-free copper-catalyzed N-arylation of nitrogen nucleophiles

Author keywords

Copper catalysis; Cross coupling; Ligand free; Nitrogen heterocycles; Sulfoximines

Indexed keywords


EID: 37349108522     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200700408     Document Type: Article
Times cited : (173)

References (49)
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    • for a ligand-free catalytic coupling, which was activated by the presence of chelating ligands, see
    • d) for a ligand-free catalytic coupling, which was activated by the presence of chelating ligands, see: A. A. Kelkar, N. M. Patil, R. V. Chaudhari, Tetrahedron Lett. 2002, 43, 7143.
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    • For selected examples, see: a
    • For selected examples, see: a) C. Bolm, O. Simic, J. Am. Chem. Soc. 2001, 123, 3830;
    • (2001) J. Am. Chem. Soc , vol.123 , pp. 3830
    • Bolm, C.1    Simic, O.2
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    • Angew1
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    • Related approaches have only been reported in the patent literature, but they have largely been uncited. For N-arylations of azoles with aryl iodides employing catalytic systems based on copper(I) iodide, see: a) U. Yasutsugu, N. Mayumi, Koei Chem. Co. Ltd, Japanese Patent Application JP 2006-342127, 2006;
    • Related approaches have only been reported in the patent literature, but they have largely been uncited. For N-arylations of azoles with aryl iodides employing catalytic systems based on copper(I) iodide, see: a) U. Yasutsugu, N. Mayumi, (Koei Chem. Co. Ltd.), Japanese Patent Application JP 2006-342127, 2006;
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    • M. Taillefer, H. J. Cristau, P. P. Cellier, J.-F. Spindler, Rhodia Chimie, Fr, French Patent Application 2859205 A1 20050304, 2005
    • b) M. Taillefer, H. J. Cristau, P. P. Cellier, J.-F. Spindler, (Rhodia Chimie, Fr.), French Patent Application 2859205 A1 20050304, 2005.
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    • While this work was in progress, an alternative N-arylation of aryl iodides using catalytic amounts of CuI was reported. There, the reaction was performed in toluene under reflux in the presence of NaOH and Bu 4NBr. In contrast to the Cu2O catalysis described here, aryl halides other than bromides showed a very low reactivity: J. W. W. Chang, X. Xu, P. W. H. Chan, Tetrahedron Lett. 2007, 48, 245
    • 2O catalysis described here, aryl halides other than bromides showed a very low reactivity: J. W. W. Chang, X. Xu, P. W. H. Chan, Tetrahedron Lett. 2007, 48, 245.
  • 45
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    • For a ligand-free bimetallic system using Fe and Cu combinations in N-arylations, see: M. Taillefer, N. Xia, A. Oualli, Angew. Chem. 2007, 119, 952;
    • For a ligand-free bimetallic system using Fe and Cu combinations in N-arylations, see: M. Taillefer, N. Xia, A. Oualli, Angew. Chem. 2007, 119, 952;
  • 46
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    • 4 led to lower yields in the N-arylation reactions. Whether DMF is acting as ligand cannot be judged.
    • 4 led to lower yields in the N-arylation reactions. Whether DMF is acting as ligand cannot be judged.
  • 48
    • 37349041125 scopus 로고    scopus 로고
    • From these two results we conclude that the active catalyst is not copper(I) iodide, which is formed during the course of the reaction
    • From these two results we conclude that the active catalyst is not copper(I) iodide, which is formed during the course of the reaction.
  • 49
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    • 2O in the N-arylation of ammonia with a 2-bromopyridine derivative performed in ethylene glycol, see: F. Lang, D. Zewge, I. N. Houpis, R. P. Volante, Tetrahedron Lett. 2001, 42, 3251.
    • 2O in the N-arylation of ammonia with a 2-bromopyridine derivative performed in ethylene glycol, see: F. Lang, D. Zewge, I. N. Houpis, R. P. Volante, Tetrahedron Lett. 2001, 42, 3251.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.