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: cw27georgetown.edu

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

DOI: 10.1055/s-0041-1738383

---

see article for more reactions

Abstract

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.

see article for more examples

---

---

Key Words

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

---

ID: J66-Y2022