Conversion of (sp(3))C-F bonds of alkyl fluorides to (sp(3))C-heteroatom (heteroatom = I, SR, SeR, TeR) bonds by the use of magnesium reagents having heteroatom substituents

Begum SA; Terao J; Kambe N

Chemistry Letters, Vol.36, No.1, 196-197, 2007

DOI10.1246/cl.2007.196 Export Citation

Conversion of (sp(3))C-F bonds of alkyl fluorides to (sp(3))C-heteroatom (heteroatom = I, SR, SeR, TeR) bonds by the use of magnesium reagents having heteroatom substituents

Begum SA, Terao J, Kambe N

A convenient method for conversion of (sp(3))C-F bonds to (sp(3))C-Z (Z = I, SR, SeR, TeR) bonds has been developed. The reaction proceeds at room temperature using magnesium salts (Z-MgX). S(N)2 mechanism for substitiution of primary alkyl fluorides with MgI2 in ether was supported by the inversion of the stereochemistry of the carbon connecting to F.