Ligands for copper-catalyzed C-N bond forming reactions with 1 mol% CuBr as catalyst

J Org Chem. 2011 May 6;76(9):3151-9. doi: 10.1021/jo1026035. Epub 2011 Mar 22.

Abstract

Several new ligands were designed to promote copper-catalyzed Ullman C-N coupling reactions. In this group, 8-hydroxyquinolin-N-oxide was found to serve as a superior ligand for CuBr-catalyzed coupling reactions of aryl iodides, bromides, and chlorides with aliphatic amines and N-heterocycles under a low catalyst loading (1% [Cu] mol). Reactions with the inexpensive catalytic system display a high functional group tolerance as well as excellent chemoselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bromides / chemistry*
  • Carbon / chemistry*
  • Catalysis
  • Copper / chemistry*
  • Ligands
  • Nitrogen / chemistry*

Substances

  • Bromides
  • Ligands
  • cupric bromide
  • Carbon
  • Copper
  • Nitrogen