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Selective Csp3-F Bond Functionalization with Lithium Iodide

Kaluvu Balaraman, Samantha Kyriazakos, Rachel Palmer, F. Yushra Thanzeel, Christian Wolf*

*Chemistry Department, Georgetown University, Washington, DC 20057, USA, Email:

K. Balaraman, S. Kyriazakos, R. Palmer, F. Y. Thanzeel, C. Wolf, Synthesis, 2022, 54, 4320-4328.

DOI: 10.1055/s-0041-1738383

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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.

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Key Words

alkyl iodides, allyl iodides, α-iodoketones, α-iodocarboxylic esters

ID: J66-Y2022