The concise synthesis of unsymmetric triarylacetonitriles via Pd-catalyzed sequential arylation: a new synthetic approach to tri- and tetraarylmethanes

Org Lett. 2015 Jan 2;17(1):50-3. doi: 10.1021/ol503213z. Epub 2014 Dec 19.

Abstract

The selective synthesis of multiarylated acetonitriles via sequential palladium-catalyzed arylations of chloroacetonitrile is reported. The three aryl groups are installed via a Pd-catalyzed Suzuki-Miyaura cross coupling reaction followed by back-to-back C-H arylations to afford triarylacetonitriles in three steps with no over-arylation at any step. The triarylacetonitrile products can be converted into highly functionalized species including tetraarylmethanes. This new strategy provides rapid access to a variety of unsymmetrical tri- and tetraarylmethane derivatives from simple, readily available starting materials.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Combinatorial Chemistry Techniques
  • Methane / analogs & derivatives*
  • Methane / chemical synthesis*
  • Methane / chemistry
  • Molecular Structure
  • Nitriles / chemical synthesis*
  • Nitriles / chemistry*
  • Palladium / chemistry*

Substances

  • Nitriles
  • Palladium
  • Methane