Direct one-pot synthesis of phenanthrenes via Suzuki-Miyaura coupling/aldol condensation cascade reaction

J Org Chem. 2008 Jan 18;73(2):495-501. doi: 10.1021/jo702001n. Epub 2007 Dec 23.

Abstract

We have developed an efficient cascade reaction, a Suzuki-Miyaura coupling followed by an aldol condensation, for the construction of phenanthrene derivatives using microwave irradiation. For example, the reaction of methyl 2-bromophenylacetamide with 2-formylphenylboronic acid in the presence of a palladium catalyst and a base provided a biaryl intermediate, which underwent in situ cyclization to afford the corresponding phenanthrene in high yield.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Ketones / chemistry*
  • Ketones / radiation effects
  • Microwaves
  • Molecular Structure
  • Organometallic Compounds / chemistry
  • Palladium / chemistry
  • Phenanthrenes / chemical synthesis*
  • Phenanthrenes / chemistry
  • Phenanthrenes / radiation effects
  • Stereoisomerism

Substances

  • Ketones
  • Organometallic Compounds
  • Phenanthrenes
  • Palladium