• Title/Summary/Keyword: Diisobutylaluminium hydride (DIBAH)

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Efficient Preparation of 3-Fluoropyrrole Derivatives

  • Kim, Bo-Mi;San, Quan-Ze;Bhatt, Lok Ranjan;Kim, Sung-Kwon;Chai, Kyu-Yun
    • Bulletin of the Korean Chemical Society
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    • v.31 no.1
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    • pp.31-34
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    • 2010
  • Noble N-substituted-3-fluoropyrroles derivatives were prepared from new precursor via ring formation. The addition reaction of ethyl iododifluoroacetate to vinyl trimethylsilane under the Cu(0) catalyst resulted in the formation of ethyl-2,2-difluoro-4-iodo-4-(trimethylsilyl)butanolate, which reacted with diisobutylaluminium hydride at $-30^{\circ}C$ to yield 2,2-diflouro-4-iodo-4-(trimethylsilyl)butanal. Finally, a series of N-substituted-3-fluoropyrrole derivatives were synthesized by the reaction of 2,2-diflouro-4-iodo-4-(trimethylsilyl)butanal with $NH_4OH$ or primary amines followed by reaction with KF solution.