Reductive cross-coupling of nonaromatic, heterocyclic bromides with aryl and heteroaryl bromides

J Org Chem. 2014 Jun 20;79(12):5771-80. doi: 10.1021/jo500905m. Epub 2014 Jun 3.

Abstract

Reductive cross-coupling allows the direct C-C bond formation between two organic halides without the need for preformation of an organometallic reagent. A method has been developed for the reductive cross-coupling of nonaromatic, heterocyclic bromides with aryl or heteroaryl bromides. The developed conditions use an air-stable Ni(II) source in the presence of a diamine ligand and a metal reductant to allow late-stage incorporation of saturated heterocyclic rings onto aryl halides in a functional-group tolerant manner.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bromides / chemistry*
  • Catalysis
  • Cross-Linking Reagents / chemistry*
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry*
  • Indicators and Reagents / chemistry*
  • Ligands
  • Metals / chemistry*
  • Molecular Structure
  • Oxidation-Reduction

Substances

  • Bromides
  • Cross-Linking Reagents
  • Heterocyclic Compounds
  • Indicators and Reagents
  • Ligands
  • Metals