Palladium-catalyzed aminocarbonylation of alkynes to succinimides

J Org Chem. 2015 Jan 2;80(1):386-91. doi: 10.1021/jo502412v. Epub 2014 Dec 1.

Abstract

Succinimide derivatives are useful building blocks for the synthesis of natural products and drugs. We describe an efficient route to succinimide derivatives comprising Pd(xantphos)Cl2-catalyzed aminocarbonylation of alkynes with aromatic or aliphatic amines in the presence of p-TsOH. The utility of this route is demonstrated with the synthesis of a large number of succinimide compounds including an important photochromic molecule.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Catalysis
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Palladium / chemistry*
  • Succinimides / chemical synthesis*
  • Succinimides / chemistry

Substances

  • Alkynes
  • Organometallic Compounds
  • Succinimides
  • Palladium