Modular synthesis of triarylmethanes through palladium-catalyzed sequential arylation of methyl phenyl sulfone

Angew Chem Int Ed Engl. 2014 Jan 13;53(3):742-6. doi: 10.1002/anie.201307019. Epub 2013 Dec 4.

Abstract

Triarylmethanes, which are valuable structures in materials, sensing and pharmaceuticals, have been synthesized starting from methyl phenyl sulfone as an inexpensive and readily available template. The three aryl groups were installed through two sequential palladium-catalyzed C-H arylation reactions, followed by an arylative desulfonation. This method provides a new synthetic approach to multisubstituted triarylmethanes using readily available haloarenes and aryl boronic acids, and is also valuable for the preparation of unexplored triarylmethane-based materials and pharmaceuticals.

Keywords: CH activation; N-heterocyclic carbenes; Suzuki-Miyaura coupling; palladium; sulfones.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Boronic Acids / chemistry
  • Carbon / chemistry
  • Catalysis
  • Dimethyl Sulfoxide / chemistry*
  • Hydrogen / chemistry
  • Methane / analogs & derivatives
  • Methane / chemistry
  • Palladium / chemistry*
  • Sulfones / chemistry*

Substances

  • Antineoplastic Agents
  • Boronic Acids
  • Sulfones
  • carbene
  • Palladium
  • Carbon
  • Hydrogen
  • dimethyl sulfone
  • Methane
  • Dimethyl Sulfoxide