Organic Letters 2009-04-16

C-F bond-cleavage reactions of fluoroalkanes with magnesium reagents and without metal catalysts.

Kouki Matsubara, Tomoka Ishibashi, Yuji Koga

Index: Org. Lett. 11(8) , 1765-68, (2009)

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Abstract

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.