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

F. NADOR; J. MANCEBO ARACIL; D. ZANOTTO; D. RUIZ MOLINA; G. RADIVOY

RSC ADVANCES

Royal Society of Chemistry

Año: 2021 vol. 11 p. 2074 - 2082

Abstract: The hydrothiolation of activated alkynes is presented as an attractive and powerful way to functionalize thiols bearing catechols. The reaction has been 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 ºC. 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 shown to be regio- and stereoselective towards the anti-Markovnikov Z-vinyl sulfide in most of the cases studied. Finally, some of the catechol derivatives obtained were tested as ligands in the preparation of coordination polymer nanoparticles (CNPs), by taking advantage of their different coordination sites with metals such as iron and cobalt.