A new method for synthesizing terminal olefins from esters using the Corey–Chaykovsky reagent

Abstract

A new method for the synthesis of terminal olefins was developed through the reaction of the Corey–Chaykovsky reagent (dimethyl-sulfonium methylide) with readily available esters. After the domino process of nucleophilic addition, elimination and rearrangement in one pot, the terminal olefins were synthesized in high yields (up to 84%) under mild conditions. The synthetic method was well tolerated by many functional groups and a new route for the synthesis of various terminal olefin derivatives is provided. In the end, a possible reaction mechanism is proposed, which is supported by DFT calculations.