Ligand-Enabled Pd(II)-Catalyzed Bromination and Iodination of C(sp3)-H Bonds

J Am Chem Soc. 2017 Apr 26;139(16):5724-5727. doi: 10.1021/jacs.7b02196. Epub 2017 Apr 13.

Abstract

We herein report the palladium(II)-catalyzed bromination and iodination of a variety of α-hydrogen-containing carboxylic acid and amino acid-derived amides. These reactions are exclusively enabled by quinoline-type ligands. The halogenated products obtained in this reaction are highly versatile and rapidly undergo further diversification. Further, we report the first example of a free carboxylic acid-directed Pd(II)-catalyzed C(sp3)-H bromination, enabled by quinoline ligands.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amides / chemistry*
  • Amino Acids / chemistry
  • Carboxylic Acids / chemistry*
  • Catalysis
  • Halogenation
  • Hydrocarbons, Brominated / chemical synthesis*
  • Hydrocarbons, Brominated / chemistry
  • Hydrocarbons, Iodinated / chemical synthesis*
  • Hydrocarbons, Iodinated / chemistry
  • Hydrogen / chemistry
  • Ligands
  • Molecular Structure
  • Palladium / chemistry*
  • Quinolines / chemistry*

Substances

  • Amides
  • Amino Acids
  • Carboxylic Acids
  • Hydrocarbons, Brominated
  • Hydrocarbons, Iodinated
  • Ligands
  • Quinolines
  • Palladium
  • Hydrogen