Polycyclic Aromatic Hydrocarbons via Iron(III)-Catalyzed Carbonyl-Olefin Metathesis

J Am Chem Soc. 2017 Mar 1;139(8):2960-2963. doi: 10.1021/jacs.7b01114. Epub 2017 Feb 21.

Abstract

Polycyclic aromatic hydrocarbons are important structural motifs in organic chemistry, pharmaceutical chemistry, and materials science. The development of a new synthetic strategy toward these compounds is described based on the design principle of iron(III)-catalyzed carbonyl-olefin metathesis reactions. This approach is characterized by its operational simplicity, high functional group compatibility, and regioselectivity while relying on FeCl3 as an environmentally benign, earth-abundant metal catalyst. Experimental evidence for oxetanes as reactive intermediates in the catalytic carbonyl-olefin ring-closing metathesis has been obtained.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry*
  • Catalysis
  • Crystallography, X-Ray
  • Ferric Compounds / chemistry*
  • Models, Molecular
  • Molecular Conformation
  • Polycyclic Aromatic Hydrocarbons / chemical synthesis*
  • Polycyclic Aromatic Hydrocarbons / chemistry

Substances

  • Alkenes
  • Ferric Compounds
  • Polycyclic Aromatic Hydrocarbons