Login / Signup

Selective Csp 3 -F Bond Functionalization with Lithium Iodide.

Kaluvu BalaramanSamantha KyriazakosRachel PalmerF Yushra ThanzeelChristian Wolf
Published in: Synthesis (2022)
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 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.
Keyphrases
  • ionic liquid
  • room temperature
  • highly efficient
  • drinking water
  • solid state
  • quantum dots
  • high resolution
  • gas chromatography