Base‐Promoted Direct Chalcogenylation of 2‐Naphthols

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 ba...

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Published inChemistrySelect (Weinheim) Vol. 4; no. 46; pp. 13558 - 13563
Main Authors Lima, David B., Santos, Pedro H. V., Fiori, Priscila, Badshah, Gul, Luz, Eduardo Q., Seckler, Diego, Rampon, Daniel S.
Format Journal Article
LanguageEnglish
Published 13.12.2019
Subjects
2-Naphthols
Bases
Direct Chalcogenylation
Transition Metal Free
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Summary: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. The fast, cheap and efficient method for direct chalcogenylation at the position 1 of 2‐naphthols with diorganoyl dichalcogenides promoted by simple bases is described. Through this easy approach, several 1‐(organochalcogeno)naphthalen‐2‐ols were prepared. The mechanistic studies suggest an electrophilic aromatic substitution and a key role of molecular oxygen.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.201903251