C−F Bond-Cleavage Reactions of Fluoroalkanes with Magnesium Reagents and without Metal Catalysts

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• 作者：Kouki Matsubara ; Tomoka Ishibashi ; Yuji Koga
• 刊名：Organic Letters
• 出版年：2009
• 出版时间：April 16, 2009
• 年：2009
• 卷：11
• 期：8
• 页码：1765-1768
• 全文大小：113K
• 年卷期：v.11,no.8(April 16, 2009)
• ISSN：1523-7052

文摘

An unexpected C−F bond-cleavage reaction of unactivated fluoroalkanes with the well-known Grignard reagents without using metal catalysts has been discovered. For example, a reaction between 1-fluorooctane and phenyl magnesium chloride gave n-octylbenzene in moderate yield. This coupling reaction via the activation of an unactivated alkyl carbon−fluorine bond proceeds with phenylmagnesium chloride, whereas methylmagnesium chloride did not give the C−C cross-coupling product but rather a halogen exchange product.