anti-Markovnikov Iodofluorination of Alkenes

Chem Asian J. 2022 May 2;17(9):e202200184. doi: 10.1002/asia.202200184. Epub 2022 Mar 22.

Abstract

The fluorination of alkenes with electrophilic N-F type reagents usually occurs through a Markovnikov-type addition, and the anti-Markovnikov-type addition may require the use of a transition metal catalyst or an expensive catalyst. Herein we describe a convenient anti-Markovnikov iodofluorination of alkenes with Selectfluor/n Bu4 NI. A wide substrate scope and good functional group tolerance were observed. The process allows for the construction of various C-F bonds, especially tertiary C-F bonds. The remarkable features make this protocol attractive, including convenient operations, simple reaction conditions, and the installation of an iodine atom which provides possibilities for further transformations.

Keywords: Alkenes; Fluorine; Iodofluorination; Tertiary C−F bonds; anti-Markovnikov Addition.

MeSH terms

  • Alkenes* / chemistry
  • Catalysis
  • Halogenation*

Substances

  • Alkenes