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Volumn 4, Issue 10, 2002, Pages 1691-1694

A copper-free Sonogashira coupling reaction in ionic liquids and its application to a microflow system for efficient catalyst recycling

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ARTICLE;

EID: 0000621561     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0257732     Document Type: Article
Times cited : (411)

References (52)
  • 2
    • 0000509322 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York
    • For reviews, see: (b) Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, pp 521-549.
    • (1991) Comprehensive Organic Synthesis , vol.3 , pp. 521-549
    • Sonogashira, K.1
  • 3
    • 0002769275 scopus 로고    scopus 로고
    • Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York
    • (c) 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
  • 4
    • 0032514972 scopus 로고    scopus 로고
    • For recent reports on the Sonogashira coupling, see: (d) Thorand, S.; Krause, N. J. Org. Chem. 1998, 63, 8551.
    • (1998) J. Org. Chem. , vol.63 , pp. 8551
    • Thorand, S.1    Krause, N.2
  • 23
    • 0347417134 scopus 로고    scopus 로고
    • For recent reviews, see: (e) Welton, T. Chem. Rev. 1999, 99, 2071.
    • (1999) Chem. Rev. , vol.99 , pp. 2071
    • Welton, T.1
  • 33
    • 0043042464 scopus 로고    scopus 로고
    • note
    • f = 0.34) to give 169 mg of diphenylacetylene (4a) (95% yield).
  • 42
    • 0043042463 scopus 로고    scopus 로고
    • note
    • The result with DMF appeared reasonable as a copper-free process. However, the reaction with aliphatic acetylenes gave low yields of the coupling products.
  • 43
    • 0041539548 scopus 로고    scopus 로고
    • note
    • 2 conducted in toluene gave a poor result (15%). For an example of a phosphine-free Sonogashira reaction, see ref 9d.
  • 51
    • 0041539547 scopus 로고    scopus 로고
    • note
    • 6] at the initial stage of the reaction, could clog the microchannels.
  • 52
    • 0043042462 scopus 로고    scopus 로고
    • note
    • We confirmed that a miniflow reactor (T-shaped tubular glass reactor, 0.2 cm i.d., 4 cm length) resulted in a low conversion of substrates, which supports highly efficient mixing as the key to the observed smooth reaction with a micromixer.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.