Efficient palladium-catalyzed double carbonylation of o-dibromobenzenes: synthesis of thalidomide

Org Biomol Chem. 2014 Aug 14;12(30):5578-81. doi: 10.1039/c4ob00796d. Epub 2014 May 22.

Abstract

We describe here a convenient and mild procedure for double carbonylation of o-dibromobenzenes with various 2-amino pyridines and naturally occurring amines, thus providing in good to excellent yields N-substituted phthalimides by using this palladium-catalyzed carbonylation procedure. Furthermore, for the first time we have applied the developed synthetic protocol for the synthesis of biologically active molecule thalidomide via a single step carbonylative cyclization reaction in excellent yield.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry
  • Bromobenzenes / chemistry*
  • Catalysis
  • Molecular Conformation
  • Palladium / chemistry*
  • Phthalimides / chemical synthesis
  • Phthalimides / chemistry
  • Thalidomide / chemical synthesis*
  • Thalidomide / chemistry

Substances

  • Amines
  • Bromobenzenes
  • Phthalimides
  • Thalidomide
  • 1,2-dibromobenzene
  • Palladium