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

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

SUBMITTER: Nador F 

PROVIDER: S-EPMC8693720 | biostudies-literature | 2021 Jan

REPOSITORIES: biostudies-literature