Bulletin of the Korean Chemical Society

  • 제31권1호
  • /
  • Pages.31-34
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  • 2010
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Efficient Preparation of 3-Fluoropyrrole Derivatives

  • 발행 : 2010.01.20
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초록

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.

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피인용 문헌

  1. From Olefination to Alkylation: In-Situ Halogenation of Julia–Kocienski Intermediates Leading to Formal Nucleophilic Iodo- and Bromodifluoromethylation of Carbonyl Compounds vol.134, pp.13, 2012, https://doi.org/10.1021/ja301601b
  2. A novel reaction of gem-difluorocyclopropyl ketones with nitriles leading to 2-fluoropyrroles vol.49, pp.84, 2013, https://doi.org/10.1039/c3cc45456h
  3. ChemInform Abstract: Efficient Preparation of 3-Fluoropyrrole Derivatives. vol.41, pp.22, 2010, https://doi.org/10.1002/chin.201022093