Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis of 2-n-Butyl-3-fluoropyrrole Derivatives

  • Kim, Bo-Mi (Department of Bionanochemistry, Wonkwang University) ;
  • San, Quan-Ze (College of Pharmacy, Yanbian University) ;
  • Bhatt, Lok Ranjan (Department of Bionanochemistry, Wonkwang University) ;
  • Jung, Dong-Woon (Department of Bionanochemistry, Wonkwang University) ;
  • Lee, Young-Hang (Department of Bionanochemistry, Wonkwang University) ;
  • Chai, Kyu-Yun (Department of Bionanochemistry, Wonkwang University)
  • Published : 2009.06.20
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Abstract

A new series of N-substituted 2-n-butyl-3-fluoropyrroles were prepared by a simple one-pot reaction designed of retrosynthesis. $\alpha,\alpha-Difluoro-\gamma-iodo-\gamma$-(trimethylsilyl)propyl n-butyl ketone, a component precursor molecule to 2-n-butyl-3-fluoropyrroles, was prepared with Cu(0) catalyst. It reacted with various primary amines to yield N-substituted 2-n-butyl-3-fluoropyrroles. The products were synthesized via a one-pot reaction scheme between $\alpha,\alpha-Difluoro-\gamma-iodo-\gamma$-(trimethylsilyl) propyl n-butyl ketone and primary amines in excess ( $\geq$ 5 molar equivalence), which eliminate the need of KF required in obtaining n-butyl-1H-3-fluoropyrrole. The yield of products depended reversely on spatial bulkness around N-binding carbon.

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References

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