Highly regioselective syntheses of substituted triphenylenes from 1,2,4-trisubstituted arenes via a co-catalyzed intermolecular alkyne cyclotrimerization

J Org Chem. 2013 Jun 7;78(11):5744-50. doi: 10.1021/jo400570b. Epub 2013 May 10.

Abstract

Herein, we report the development of a new method for the syntheses of substituted triphenylenes from the corresponding 1,2,4-trisubstituted arenes, which were themselves generated in a highly regioselective manner according to an intermolecular alkyne cyclotrimerization reaction that was catalyzed by a novel Co-TMTU complex. This highly regioselective reaction for the formation of 1,2,4-trisubstituted arenes will be a valuable addition to the plethora of tools already available to synthetic chemists and encourage further mechanistic studies of this important alkyne trimerization process.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Catalysis
  • Chrysenes / chemical synthesis*
  • Chrysenes / chemistry
  • Cobalt / chemistry*
  • Cyclization
  • Molecular Structure
  • Stereoisomerism

Substances

  • Alkynes
  • Chrysenes
  • triphenylene
  • Cobalt