Thiol-yne click reaction: an interesting way to derive thiol-provided catechols

• DOI: 10.1039/d0ra09687c
• Publication Date: 2021-01-07T09:10:04Z
• Authors: Fabiana Nador; Juan Mancebo-Aracil; Duham Zanotto; Daniel Ruiz-Molina; Gabriel Radivoy
• Keywords: Catechol; Thiol; Markovnikov's rule

The hydrothiolation of activated alkynes is presented as an attractive and powerful way to functionalize thiols bearing catechols. reaction was promoted by a heterogeneous catalyst composed copper nanoparticles supported on TiO2 (CuNPs/TiO2) in 1,2-dichloroethane (1,2-DCE) under heating at 80 °C. could be recovered reused three consecutive cycles, showing slight decrease its catalytic activity. Thiol derivatives catechol moieties, obtained through versatile Michael addition, were reacted with different alkynes, such methyl propiolate, propiolic acid, propiolamide or 2-ethynylpyridine. shown regio- stereoselective towards anti-Markovnikov Z-vinyl sulfide most cases studied. Finally, some tested ligands the preparation coordination polymer (CNPs), taking advantage their sites metals iron cobalt.