Ligand effects in the synthesis of N-heterocycles by intramolecular Heck reactions

J Org Chem. 2006 Feb 17;71(4):1732-5. doi: 10.1021/jo0522660.

Abstract

Chemo- and regioselectivity of intramolecular Heck reactions are dependent on the type of ligand employed. Six- to eight-membered benzolactams are produced in good yields using PPh3 as ligand. In contrast, a biaryl coupling occurred preferentially under ligandless conditions to form a dihydrophenanthridine product. Conformations of the seven- and eight-membered benzolactams in the solid state were examined by X-ray crystallography.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzene Derivatives / chemical synthesis
  • Crystallography, X-Ray
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Lactams / chemical synthesis
  • Ligands
  • Molecular Conformation
  • Nitrogen*

Substances

  • Benzene Derivatives
  • Heterocyclic Compounds
  • Lactams
  • Ligands
  • Nitrogen