Copper-catalyzed trichloromethylative carbonylation of ethylene

Abstract

Difunctionalization of alkenes is an efficient strategy for the synthesis of complex compounds from readily available starting materials. Herein, we developed a copper-catalyzed visible-light-mediated trichloromethylative carbonylation of ethylene by employing commercially available CCl₄ and CO as trichloromethyl and carbonyl sources, respectively. With this protocol, various nucleophiles including amines, phenols, and alcohols can be rapidly transformed into β-trichloromethyl carboxylic acid derivatives with good functional-group tolerance. Bis-vinylated γ-trichloromethyl amides can also be obtained by adjusting the pressure of carbon monoxide and ethylene. In addition, this photocatalytic system can be successfully applied in the late-stage functionalization of bioactive molecules and pharmaceutical derivatives as well.