The synthesis of fluorinated α-pyrans via

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• 作者：Donald J. Burton ; Steven W. Hansen
• 关键词：F-vinylcopper reagents ; F-dienylcopper reagents ; Fluorinated α ; -pyrans ; Stereospecific addition ; Acylation
• 刊名：Journal of Fluorine Chemistry
• 出版年：2009
• 出版时间：September 2009
• 年：2009
• 卷：130
• 期：9
• 页码：775-779
• 全文大小：301 K

文摘

Fluorinated vinylcopper reagents were prepared in situ via reaction of fluorinated vinylbromides or iodides with cadmium or zinc powder followed by metathesis with Cu(I)Br. Hexafluoro-2-butyne was then added to the solution of the F-vinylcopper reagent which resulted in a stereospecific syn addition of the F-vinylcopper reagent to the alkyne to provide in situ the corresponding dienylcopper reagent. Subsequent acylation of the dienylcopper reagent gave a dienylketone, which spontaneously cyclized to the 2H-pyran. This methodology provides a useful one flask route to fluorinated 2H-pyrans.