The alkynylation of naphthols takes place with total regiocontrol at the peri position of the hydroxyl group in the presence of [RuCl2(p-cymene)]2 as the catalyst. This reaction features high functional group tolerance. The related ortho-alkynylation of benzoic acids proceeds under similar conditions and also shows wide functional group tolerance. Both reactions proceed through metalation, insertion of the alkyne, and bromide elimination.

Formaldehyde (FA) is a ubiquitous endogenous and environmental metabolite that is thought to exert cytotoxicity through DNA and DNA-protein crosslinking, likely contributing to the onset of the human DNA repair condition Fanconi Anaemia. Mutations in the genes coding for FA detoxifying enzymes underlie a human inherited bone marrow failure syndrome (IBMFS), even in the presence of functional DNA repair, raising the question of whether FA causes relevant cellular damage beyond genotoxicity. Here, we report that FA triggers cellular redox imbalance in human cells and in Caenorhabditis elegans. Mechanistically, FA reacts with the redox-active thiol group of glutathione (GSH), altering the GSH:GSSG ratio and causing oxidative stress. FA cytotoxicity is prevented by the enzyme alcohol dehydrogenase 5 (ADH5/GSNOR), which metabolizes FA-GSH products, lastly yielding reduced GSH. Furthermore, we show that GSH synthesis protects human cells from FA, indicating an active role of GSH in preventing FA toxicity. These findings might be relevant for patients carrying mutations in FA-detoxification systems and could suggest therapeutic benefits from thiol-rich antioxidants like N-acetyl-L-cysteine.

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Comparative studies were carried out with the addition of different silver salts. Our results indicate that the bulkier complex is the most effective and that the addition of methanol as co-solvent not only shortens reaction times but also stabilizes the less bulky complexes.

Water-soluble gold(I) N-heterocyclic carbene complexes were synthesized and characterized using X-ray absorption spectroscopy (XAFS) in combination with traditional analytical techniques such as NMR, mass spectrometry, and UV–vis spectroscopy. XANES and EXAFS regions are sensitive to coordination number, ligand electronic structure, and distance around the metal center, providing information on the oxidation state and bonding structure of gold, which allows discrimination between mono- and bis-carbene species. Preliminary results showed that the catalysts are active in the hydration of terminal alkynes in aqueous media; in addition, they are highly recyclable.