The Concise Synthesis of Unsymmetric Triaryl­acetonitriles via Pd‑Catalyzed Sequential Arylation: A New Synthetic Approach to Tri- and Tetraarylmethanes

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