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

CAPURSO, MATÍAS; RADIVOY, GABRIEL; NADOR, FABIANA; DORN, VIVIANA

Basilea

Congreso; 26th International Electronic Conference on Synthetic Organic Chemistry,; 2022

A recently published article by our research group demonstrated that the hydrothiolation of ac-tivated 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 an-ti-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 investi-gated through DFT studies. Theoretical results and experimental data were consistent with a re-action mechanism based on a copper-catalyzed anti-Markovnikov hydrothiolation process that favors the formation of the Z-vinyl sulfide.