Expedient synthesis of phenanthrenes via In(III)-catalyzed 6-exo-dig cycloisomerization

Org Lett. 2013 Feb 15;15(4):920-3. doi: 10.1021/ol400073s. Epub 2013 Feb 1.

Abstract

This paper documents the first example of In(III)-catalyzed selective 6-exo-dig hydroarylation of o-propargylbiaryls and their subsequent double-bond migration to obtain functionalized phenanthrenes. Electron-rich biaryl substrates undergo hydroarylation more effectively, and the substrates with various types of substituents on the alkyne can also be smoothly and selectively converted to phenanthrenes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Biphenyl Compounds / chemistry*
  • Catalysis
  • Cyclization
  • Indium / chemistry*
  • Molecular Structure
  • Phenanthrenes / chemical synthesis*
  • Phenanthrenes / chemistry
  • Stereoisomerism

Substances

  • Alkynes
  • Biphenyl Compounds
  • Phenanthrenes
  • Indium