Pd catalyzed insertion of alkynes into cyclic diaryliodoniums: a direct access to multi-substituted phenanthrenes

Org Biomol Chem. 2015 Nov 7;13(41):10386-91. doi: 10.1039/c5ob01597a.

Abstract

Cyclic diaryliodoniums remain unexplored compared to linear iodoniums. In our current work, internal alkynes were for the first time applied to react with cyclic iodoniums, catalyzed by Pd, resulting in a [4 + 2] benzannulation. Our work offers a new strategy to synthesize multi-substituted phenanthrene derivatives which are not easily accessed by conventional methods.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Catalysis
  • Cyclization
  • Molecular Structure
  • Onium Compounds / chemistry*
  • Organometallic Compounds / chemistry*
  • Palladium / chemistry*
  • Phenanthrenes / chemical synthesis*
  • Phenanthrenes / chemistry

Substances

  • Alkynes
  • Onium Compounds
  • Organometallic Compounds
  • Phenanthrenes
  • Palladium