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Synlett 2001; 2001(5): 0649-0651
DOI: 10.1055/s-2001-13390
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A Highly Effective Pd/Cu-Catalyzed Coupling Reaction of Terminal Alkynes with Organic Halides Promoted by Tetrabutylammonium Fluoride or Hydroxide

Atsunori Mori* , Tomohiro Shimada, Tatsuhiro Kondo, Akitoshi Sekiguchi
  • *Chemical Resources Laboratory, Tokyo Institute of Technology, Nagatsuta, Yokohama 226-8503, Japan; Fax + 81-4 59 24 52 24; E-mail: amori@res.titech.ac.jp
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Publication Date:
31 December 2001 (online)

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Coupling reaction of terminal alkynes catalyzed by Pd/Cu with several organic electrophiles is shown to proceed by use of tetrabutylammonium fluoride (TBAF) or tetrabutylammonium hydroxide (TBAOH) as an activator. Treatment of 1-octyne and 4-methoxy-iodobenzene in the presence of 2.0 equiv of TBAOH, 1 mol% of PdCl2(PPh3)3, and 2 mol% of CuI affords 1-phenyl-1-octyne in 98% yield after stirring at room temperature for 1 h. The new coupling reaction is also applied to polymer synthesis via polycondensation of a diyne and a diiodoarene.

Sonogashira-Hagihara coupling - Pd/Cu catalyst - terminal alkynes - tetrabutylammonium fluoride - tetrabutylammonium hydroxide - polycondensation

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