Background: Synthesis of many organic compounds through oxygenation and sulfurization, which involves the formation of carbon-oxygen and carbon-sulfur bonds, is a widely used method in organic chemistry. Extensive studies have been conducted to develop novel methods for forming these bonds. However, issues such as the poisoning of metal catalysts by sulfur-containing compounds have hindered further progress in these studies. Therefore, the use of alternative methods for metal catalysts has garnered significant attention. Triphenylphosphine, as a tertiary phosphine with nucleophilic properties, can act as a catalyst in various reactions. The reaction of triphenylphosphine with activated carbon-carbon multiple bonds and the formation of dipolar ion intermediates can initiate various organic reactions, including oxygenation and sulfurization. This compound is considered a suitable alternative to metal catalysts. Additionally, triphenylphosphine is recognized as an important ligand in both inorganic and organic chemistry. Other advantages of this catalyst include its low cost and high stability.
Objective: The aim of this research is to form carbon-oxygen and carbon-sulfur bonds in the synthesis of β-thiopropionate esters. The stable and inexpensive triphenylphosphine is used as a catalyst in these reactions.
Methodology: This research project involves a two-step, one-pot reaction. In the first step, maleic anhydride undergoes ring-opening with an alcohol in the presence of triphenylphosphine catalyst, forming a carbon-oxygen bond and producing acrylate. In the second step, the Michael addition of thiol to the acrylate occurs, forming a carbon-sulfur bond. Initially, the reaction conditions were optimized by examining various solvents, temperatures, and different amounts of catalyst and starting materials. Subsequently, with the best conditions obtained, various β-thiopropionate ester derivatives were synthesized using different alcohols and thiols.
Outcome: The synthes
