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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 31, Number 1
BKCSDE 31(1)
January 20, 2010 

Efficient Preparation of 3-Fluoropyrrole Derivatives
Bo Mi Kim, Quan Ze San, Lok Ranjan Bhatt, Sung Kwon Kim, Kyu Yun Chai*
2,2-Difluoro-4-iodo-4-(trimethylsilyl)butanal, β-Fluoropyrrole, 3,3-Difluoro-5-(trimethylsilyl) pyrrolidin-2-ol, Diisobutylaluminum hydride (DIBAH)
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 oC 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 NH4OH or primary amines followed by reaction with KF solution.
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