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DOI: 10.1055/s-0043-1774905
Iodine(III)-Mediated Ring-Contraction Reactions Using Halogenated and Non-halogenated Solvents
The authors thank the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES), Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP), Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) and the Institute of Chemistry, University of São Paulo, Brazil. This research work was supported by Researchers Supporting Project Number (RSP2024R45) at King Saud University, Riyadh, Saudi Arabia.
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Luiz F. Silva Jr. In memoriam.
Abstract
The transformation of a six-membered ring into the corresponding five-membered product is an important synthetic approach used in medicinal chemistry and industrial technologies. However, the yield of the product obtained through a simple one-step reaction is lower in some reported solvent systems. Here, we present the ring contraction of 1,2-dihydronaphthalene derivatives into the corresponding indanes using an environmentally friendly reagent hydroxy(tosyloxy)iodobenzene (HTIB). This transformation is achieved in both non-halogenated and halogenated solvents. We show that the halogenated solvent system not only increased the yield of the anticipated product but also reduced the formation of by-products. This study delivers an important development regarding the effectiveness of hypervalent iodine reagents in halogenated and non-halogenated solvents for ring-contraction reactions.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2204-8461.
- Supporting Information
Publikationsverlauf
Eingereicht: 24. März 2024
Angenommen nach Revision: 14. Mai 2024
Artikel online veröffentlicht:
28. Mai 2024
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