2500-88-1Relevant articles and documents
Thiol-yne click reaction: an interesting way to derive thiol-provided catechols
Nador, Fabiana,Mancebo-Aracil, Juan,Zanotto, Duham,Ruiz-Molina, Daniel,Radivoy, Gabriel
, p. 2074 - 2082 (2021)
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. Finally, some catechol derivatives obtained were tested as ligands in the preparation of coordination polymer nanoparticles (CNPs), by taking the advantage of their different coordination sites with metals such as iron and cobalt.
Practical and efficient recyclable oxidative system for the preparation of symmetrical disulfides under aerobic conditions
Ling, Ong Chiu,Heidelberg, Thorsten,Ching, Juan Joon,Khaligh, Nader Ghaffari
, p. 281 - 294 (2020/12/13)
An efficient and practical oxidative coupling of thiols to symmetrical disulfides is developed at room temperature under aerobic conditions. The commercially available sodium methoxide solution 30 wt. % in methanol together with the air was used as a retrievable promoter system and green oxidant, respectively, for the preparation of symmetrical disulfides. The desired products were obtained in good to high yields by an economical procedure. No overoxidation of the symmetrical disulfides was observed, and various functional groups were well tolerated in the current protocol. Moreover, the new reagent reduces the generation of hazardous waste due to its high reusability. The reaction proceeded in the absence of light, and it was not inhibited by TEMPO. Also, the low yield of TEMPO-benzyl thiol adduct was detected under these conditions. Based on our experiments, a possible mechanism was proposed in the absence and presence of TEMPO.
Aerobic oxidation of thiols to disulfides under ball-milling in the absence of any catalyst, solvent, or base
Chatterjee, Tanmay,Ranu, Brindaban C.
, p. 10680 - 10686 (2013/09/02)
An efficient aerobic chemoselective oxidation of thiols to disulfides has been achieved under ball-milling over neutral aluminium oxide (grinding auxiliary) in the absence of any catalyst, co-oxidant, solvent, or base. A wide variety of functionalized diaryl, diheteroaryl and dialkyl disulfides have been obtained in high yields. The Royal Society of Chemistry 2013.
