The functionalisation of 2-naphthols and their derivatives has much importance because of their potential pharmaceutical and materials applications. In this context, this work presents a fast, cheap, and efficient method for direct chalcogenylation at position C1 of 2-naphthols promoted by simple bases. The mechanistic studies indicate an ionic mechanism, essentially an electrophilic aromatic substitution, with a key role played by atmospheric oxygen for regeneration of the diorganoyl dichalcogenides.
Transition metal catalysed direct sulfanylations of unreactive C-H bonds have become a unique and straightforward synthetic strategy in late-stage C-S bond formation of relevant complex molecules. Such transformations have represented...
A transition-metal-free one-pot synthesis of 3-halo-2-organochalcogenylbenzo[b]chalcogenophenes has been developed using 1-(2-organochalcogenylethynyl)-2-butylchalcogenylbenzenes generated in situ from 1-(2,2-dibromovinyl)-2-organochalcogenylbenzenes and diorganoyl dichalcogenides. By this method, several 2,3-disubstituted benzo[b]chalcogenophenes were prepared in yields of 48-93%. The mechanistic investigation suggests that the formation of chalcogenoacetylenes containing an adjacent chalcogen atom in the first step of this one-pot procedure involves acetylide anions formed from 1-(2,2-dibromovinyl)-2-organochalcogenylbenzenes and mild bases.
We have developed an efficient chalcogenylation of electron-rich naphthalene derivatives catalyzed by FeCl3 and KI. The methodology provides access to several nonsymmetrical diorganoyl chalcogenides (S, Se) by selective C1 chalcogenylation of 2-naphthols or 2-naphthylamines using simple and cheap catalysts. Several control experiments supported the hypothesis that a redox reaction between Fe(III) and KI produces I2, which catalyzed the chalcogenylation.
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