Abstract
A highly efficient method for C–F bond functionalization of a broad variety of activated
and unactivated aliphatic substrates with inexpensive lithium iodide is presented.
Primary, secondary, tertiary, benzylic, propargylic and α-functionalized alkyl fluorides
react in chlorinated or aromatic solvents at room temperature or upon heating to give
the corresponding iodides, which are isolated in 91–99% yield. The reaction is selective
for aliphatic monofluorides and can be coupled with in situ nucleophilic iodide replacements to install carbon–carbon, carbon–nitrogen, and carbon–sulfur
bonds with high yields. Alkyl difluorides, trifluorides, even in activated benzylic
positions, are inert under the same conditions and aryl fluoride bonds are also tolerated.
Key words
C–F bond functionalization - alkyl fluorides - halide exchange - nucleophilic substitution
- lithium iodide
