Synthesis of a Fluoro-Sulfonium Ylide Derivative for the Study of Carbene Intermediates

Abstract

Carbenes are unstable carbon based molecules that are common intermediates in high-energy chemical reactions and play a role in the synthesis of valuable target molecules such as carbohydrates. Carbenes have the ability to form carbon-carbon bonds through metal catalyzed cross coupling reactions. These reactions are important tools in organic synthesis, and allow for the formation of products including pharmaceuticals, dyes, and agrochemicals.The study of carbene intermediates and their unique characteristics may provide further insight into medicine and other advancements in science. A four step synthetic pathway was proposed to generate derivatives of dibenzyldione carbene intermediates. This work highlights progress towards the synthesis of 1,3-di-(4-fluorophenyl)-1,3-dione sulfonium ylide, a carbene precursor. Using published protocols as a guide, two synthetic intermediates, 4-fluorobenzoyl chloride and 1,3-di-(4-fluorophenyl)-1,3-propanedione, were successfully synthesized, isolated, and characterized by various spectroscopic techniques including 1H NMR, GC-MS, and IR spectroscopy. These derivatives could provide valuable insights into the electronic structure and reactivity of carbene intermediates.