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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 30, Number 6
BKCSDE 30(6)
June 20, 2009 

Synthesis of 2-n-Butyl-3-fluoropyrrole Derivatives
Bo Mi Kim, Quan Ze San, Lok Ranjan Bhatt, Dong Woon Jung, Young Hang Lee, Kyu Yun Chai*
N-Substituted 2-n-butyl-3-fluoropyrroles, α,α-Difluoro-iodomethyl n-butylketone, 2,α,α-Difluoro-γ-iodo-γ-(trimethylsilyl)propyl n-butylketone, 2-Butyl-3,3-difluoro-5-trimethylsilyl pyrroline
A new series of N-substituted 2-n-butyl-3-fluoropyrroles were prepared by a simple one-pot reaction designed of retrosynthesis. ?α,α-Difluoro-γ-iodo-γ-(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 α,α-Difluoro-γ-iodo-γ-(trimethylsilyl) propyl n-butyl ketone and primary amines in excess ( ≥ 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.
1293 - 1296
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