Selective Synthesis of Fluorinated Furan Derivatives via AgNO3-Catalyzed Activation of an Electronically Deficient Triple Bond

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• 作者：Satoru Arimitsu ; Gerald B. Hammond
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：October 26, 2007
• 年：2007
• 卷：72
• 期：22
• 页码：8559 - 8561
• 全文大小：82K
• 年卷期：v.72,no.22(October 26, 2007)
• ISSN：1520-6904

文摘

The transition metal-catalyzed direct activation of electrondeficient triple bonds was investigated by using the combinedelectron withdrawing effects of two fluorine atoms tomodulate the electronic density of the triple bond. With useof catalytic amounts of AgNO₃ (10 mol %) the synthesis ofsubstituted 3,3-difluoro-4,5-dihydrofurans from gem-difluorohomopropargyl alcohols occurred in excellent NMR yields.Treatment of these dihydrofurans with SiO₂ or Pd/H₂ yieldedthe corresponding 3-fluorinated furans and 3,3-difluorotetrahydrofurans.