Fluorination of aryl boronic acids using acetyl hypofluorite made directly from diluted fluorine

J Org Chem. 2013 Dec 6;78(23):11794-7. doi: 10.1021/jo401832f. Epub 2013 Nov 13.

Abstract

Aryl boronic acids or pinacol esters containing EDG were converted in good yields and fast reactions to the corresponding aryl fluorides using the readily obtainable solutions of AcOF. In reactions with aryl boronic acids containing EWG at the para position, there are two competing forces: one directing the fluorination to take place ortho to the boronic acid and the other, toward an ipso substitution. With EWG meta to the boronic acid, substitution ipso to the boron moiety takes place in good yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / chemistry*
  • Boronic Acids / chemistry*
  • Esters / chemistry
  • Fluorine / chemistry*
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Hydrocarbons, Fluorinated / chemistry
  • Molecular Structure

Substances

  • Acetates
  • Boronic Acids
  • Esters
  • Hydrocarbons, Fluorinated
  • Fluorine
  • acetyl hypofluorite