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Sonogashira–Hagihara Coupling towards Diaryl Alkynes Catalyzed by FeCl3⋅6 H2O/Cationic 2,2'-Bipyridyl

Authors

  • Tzu-Ting Hung,

    1. Institute of Organic and Polymeric Materials, National Taipei University of Technology, 1, Sec. 3, Chung-Hsiao E. Rd., Taipei 106 (Taiwan), Fax: (+886) 2-2731-7174
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  • Chun-Min Huang,

    1. Institute of Organic and Polymeric Materials, National Taipei University of Technology, 1, Sec. 3, Chung-Hsiao E. Rd., Taipei 106 (Taiwan), Fax: (+886) 2-2731-7174
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  • Prof. Fu-Yu Tsai

    Corresponding author
    1. Institute of Organic and Polymeric Materials, National Taipei University of Technology, 1, Sec. 3, Chung-Hsiao E. Rd., Taipei 106 (Taiwan), Fax: (+886) 2-2731-7174
    • Institute of Organic and Polymeric Materials, National Taipei University of Technology, 1, Sec. 3, Chung-Hsiao E. Rd., Taipei 106 (Taiwan), Fax: (+886) 2-2731-7174
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Abstract

Efficient and environmentally benign one-pot Sonogashira–Hagihara coupling of aryl iodides with 4-aryl-2-methylbut-3-yn-2-ols catalyzed by an FeCl36 H2O/cationic 2,2'-bipyridyl system in water under air in the presence of zinc powder reductant was performed. Various aryl iodides and 4-aryl-2-methylbut-3-yn-2-ols were used as reactants, which afforded moderate to high yields of cross-coupled products. Although alkyl-substituted 2-methylbut-3-yn-2-ol could not be coupled with aryl iodides, the use of alkyl terminal alkynes under similar conditions provided the corresponding products in moderate yields. This reaction protocol was also used to synthesize both symmetric and asymmetric 1,4-diarylbuta-1,3-diynes. This one-pot iron-catalyzed Sonogashira–Hagihara coupling reaction progressed without the use of an organic solvent, a copper cocatalyst, or an inert atmosphere, rendering it an environmentally friendly method with potential for practical applications.

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