C-F bond-cleavage reactions of fluoroalkanes with magnesium reagents and without metal catalysts.
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.
Matsubara
Kouki
K
Department of Chemistry, Faculty of Science, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan.
Ishibashi
Tomoka
T
Koga
Yuji
Y