Reductive Cleavage of 2,2,2-Trichloroethyl Esters by Titanocene Catalysis

Abstract

Esters are of widespread use for protecting carboxylic acids in organic synthesis. However, methods to cleave esters often employ harsh conditions. Herein, we report a new and mild method for the reductive cleavage of 2,2,2-trichloroethylesters (TCE esters). Our radical method employs Cp2TiCl as an electron transfer catalyst and Zn dust as stoichiometric reducing agent. It avoids the use of strong Brønstedt-acids as well as aqueous conditions and can be carried out at room temperature.

Keywords

• Catalysis
• Protecting groups
• Radicals
• Synthesis
• Titanocenes