“TYC” Reaction between Alkynes and Catechol-Thiol Derivatives Prompted by Metal Nanocatalysis: Mechanism Study by DFT Calculation

Abstract

A recently published article by our research group demonstrated that the hydrothiolation of activated alkynes is a successful way to functionalize thiols bearing catechols. The reaction was promoted by the CuNPs/TiO2 nanocatalyst and was regio- and stereoselective towards the anti-Markovnikov Z-vinyl sulfide with good to excellent yields (47–97%). The scope of the reaction was evaluated and, based on experimental observations, the reaction mechanism was investigated through DFT studies. Theoretical results and experimental data were consistent with a reaction mechanism based on a copper-catalyzed anti-Markovnikov hydrothiolation process that favors the formation of the Z-vinyl sulfide.

Keywords

• hydrothiolation
• DFT
• computational chemistry