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Synthesis of allyl iodides

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The use of a CeCl37H2O/NaI system in acetonitrile enables an exceedingly mild preparation of iodides from alcohols. The simplicity of this approach, the low cost of reagents, and the ease of use display the attractiveness of the present method for a wide variety of alcohols.
M. Di Deo, E. Marcantoni, E. Torregiani, G. Bartoli, M. C. Bellucci, M. Bosco, L. Sambri, J. Org. Chem., 2000, 65, 2830-2833.


Primary, secondary, tertiary, benzylic, propargylic and α-functionalized alkyl fluorides react in chlorinated or aromatic solvents at room temperature or upon heating with inexpensive lithium iodide to give the corresponding iodides in very good yields. The reaction is selective for aliphatic monofluorides and can be coupled with in situ nucleophilic iodide replacements.
K. Balaraman, S. Kyriazakos, R. Palmer, F. Y. Thanzeel, C. Wolf, Synthesis, 2022, 54, 4320-4328.