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Volumn 3, Issue 15, 2001, Pages 2419-2421

Synthesis of differentially substituted hexaethynylbenzenes based on tandem sonogashira and Negishi cross-coupling reactions

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ARTICLE;

EID: 0001096422     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016274o     Document Type: Article
Times cited : (124)

References (37)
  • 10
    • 0001083913 scopus 로고    scopus 로고
    • For recent reviews, see: (c) Haley, M. M. Synlett 1998, 557.
    • (1998) Synlett , pp. 557
    • Haley, M.M.1
  • 20
    • 0002769275 scopus 로고    scopus 로고
    • Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York
    • For a review see: (b) Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 1998; pp 203-229.
    • (1998) Metal-catalyzed Cross-coupling Reactions , pp. 203-229
    • Sonogashira, K.1
  • 25
    • 0343471420 scopus 로고    scopus 로고
    • The synthesis of 9 and its derivatives has been accomplished by the use of expensive trifluorotriazine (with ethynyllithium reagents: ref 12 and Wortmann, R.; Glania, C.; Krämer, P.; Matschiner, R.; Wolff, J. J.; Kraft, S.; Treptow, B.; Barbu, E.; Längle, D.; Görlitz, G. Chem. Eur. J. 1997, 3, 1765) or a potentially toxic ethynyltin reagent (with trichlorotriazine 8: Faust, R.; Göbelt, B. Tetrahedron Lett. 1997, 38, 8017.).
    • (1997) Tetrahedron Lett. , vol.38 , pp. 8017
    • Faust, R.1    Göbelt, B.2
  • 26
    • 0042539631 scopus 로고    scopus 로고
    • note
    • We employed ca. 40% toluene as a cosolvent with THF to raise the reflux temperature.
  • 27
    • 0042539630 scopus 로고    scopus 로고
    • note
    • As a byproduct, pentakis[(trimethylsilyl)ethynyl]benzene (7) was isolated in 10% yield (see ref 11b).
  • 30
    • 0033534423 scopus 로고    scopus 로고
    • For recent examples of palladium-catalyzed coupling of unactivated chloroarenes, see: (a) Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10.
    • (1999) J. Org. Chem. , vol.64 , pp. 10
    • Littke, A.F.1    Fu, G.C.2
  • 35
    • 0034812321 scopus 로고    scopus 로고
    • Recently the utility of zinc reagents in palladium-catalyzed cross-coupling reactions of aryl chlorides was reported by Fu. However, alkynylzinc reagents were reported to be unsuitable coupling partners: Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 2719
    • Dai, C.1    Fu, G.C.2


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