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Volumn 129, Issue 32, 2007, Pages 9844-9845

Iron-catalyzed selective biaryl coupling: Remarkable suppression of homocoupling by the fluoride anion

Author keywords

[No Author keywords available]

Indexed keywords

ANION; FLUORIDE; IRON;

EID: 34547873501     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja073084l     Document Type: Article
Times cited : (264)

References (29)
  • 4
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    • Ivica, C, Ed, Elsevier Ltd: Oxford
    • (d) Ivica, C., Ed. Synthesis of Biaryls; Elsevier Ltd: Oxford, 2004.
    • (2004) Synthesis of Biaryls
  • 5
    • 34547872125 scopus 로고    scopus 로고
    • de Meijere, A, Diederich, F, Eds, 2nd ed, Wiley-VCH: New York
    • (a) de Meijere, A., Diederich, F., Eds. Metal-Catalyzed Cross-coupling Reactions, 2nd ed.; Wiley-VCH: New York, 2004.
    • (2004) Metal-Catalyzed Cross-coupling Reactions
  • 10
    • 0037146041 scopus 로고    scopus 로고
    • Selected recent papers: (a) Fürstner, A.; Leitner, A.; Méndez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856.
    • Selected recent papers: (a) Fürstner, A.; Leitner, A.; Méndez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856.
  • 19
    • 34547882899 scopus 로고    scopus 로고
    • Heteroaromatic compounds undergo cross-coupling: see ref 4a,b
    • Heteroaromatic compounds undergo cross-coupling: see ref 4a,b.
  • 20
    • 33644770072 scopus 로고    scopus 로고
    • Favorable effects of NHC ligands in iron-catalyzed cross-couplings of haloalkanes were reported. (a) Bica, K.; Gaertner, P. Org. Lett. 2006, 8, 733.
    • Favorable effects of NHC ligands in iron-catalyzed cross-couplings of haloalkanes were reported. (a) Bica, K.; Gaertner, P. Org. Lett. 2006, 8, 733.
  • 22
    • 34547893577 scopus 로고    scopus 로고
    • Other NHC or phosphine ligands are not effective. See Supporting Information for details
    • Other NHC or phosphine ligands are not effective. See Supporting Information for details.
  • 23
    • 34547864376 scopus 로고    scopus 로고
    • 3 also gave the homocoupling product 4 as a major product.
    • 3 also gave the homocoupling product 4 as a major product.
  • 24
    • 0037090932 scopus 로고    scopus 로고
    • In situ generation of NHC ligand, see:, Int. Ed, and references cited therein
    • In situ generation of NHC ligand, see: Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290 and references cited therein.
    • (2002) Angew. Chem , vol.41 , pp. 1290
    • Herrmann, W.A.1
  • 26
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    • 3]: (a) Alonso, P. J.; Arauzo, A. B.; Forniés, J.; Garcia-Monforte, M. A.; Martin, A.; Martinez, J. I.; Menjón, B.; Rillo, C.; Sáiz-Garitaonandia, J. J. Angew. Chem., Int. Ed. 2006, 44, 6707.
    • 3]: (a) Alonso, P. J.; Arauzo, A. B.; Forniés, J.; Garcia-Monforte, M. A.; Martin, A.; Martinez, J. I.; Menjón, B.; Rillo, C.; Sáiz-Garitaonandia, J. J. Angew. Chem., Int. Ed. 2006, 44, 6707.
  • 27
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    • 2: (b) Fürstner, A.; Krause, H.; Lehmann, C. Angew. Chem., Int. Ed. 2006, 45, 440.
    • 2: (b) Fürstner, A.; Krause, H.; Lehmann, C. Angew. Chem., Int. Ed. 2006, 45, 440.
  • 28
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    • Fe-F complex: (c) Vela, J.; Smith, J. M.; Yu, Y.; Ketterer, N. A.; Flaschenriem, C. J.; Lachicotte, R. J.; Holland, P. L. J. Am. Chem. Soc. 2005, 127, 7857.
    • Fe-F complex: (c) Vela, J.; Smith, J. M.; Yu, Y.; Ketterer, N. A.; Flaschenriem, C. J.; Lachicotte, R. J.; Holland, P. L. J. Am. Chem. Soc. 2005, 127, 7857.
  • 29
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    • 2, etc.) produced significant amounts of homocoupling products 3 and 4 (6-30% yields) and reduced the cross-coupling product yield.
    • 2, etc.) produced significant amounts of homocoupling products 3 and 4 (6-30% yields) and reduced the cross-coupling product yield.


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