ABSTRACT
Herein, we report an oxygen insertion in activated ketones from simple inorganic carbonates for the synthesis of symmetric aromatic anhydrides. For the first time, Li2CO3 acts as an oxygen source and the in situ generated symmetric aromatic anhydrides undergo Pummerer-type rearrangement to access α-benzoyloxy-thioethers. Attractively, this protocol occurs under metal-, ligand-, and oxidant-free conditions and is compatible with a wide range of substrates. Control experiments reveal the reaction pathway.
ABSTRACT
Imidazolium salts have been effectively employed as suitable acyl transfer agents in amidation and esterification in organic synthesis. The weak acyl C(O)-C imidazolium bond was exploited to generate acyl electrophiles, which further react with amines and alcohols to afford amides and esters. The broad substrate scope of anilines and benzylic amines and base-promoted conditions are the benefits of this route. Interestingly, phenol, benzylic alcohols, and a biologically active alcohol can also be subjected to esterification under the optimized conditions.
ABSTRACT
Organomercurials including methylmercury are ubiquitous environmental pollutants and highly toxic to humans. Now it could be shown that N-methylimidazole based thiones/selones having an N-CH2CH2OH substituent are remarkably effective in detoxifying various organomercurials to produce less toxic HgE (E=S, Se) nanoparticles. Compounds lacking the N-CH2CH2OH substituent failed to produce HgE nanoparticles upon treatment with organomercurials, suggesting that this moiety plays a crucial role in the detoxification by facilitating the desulfurization and deselenization processes. This novel way of detoxifying organomercurials may lead to the discovery of new compounds to treat patients suffering from methylmercury poisoning.
