Indium(III)-Catalyzed Synthesis of Benzo[ b]furans by Intramolecular Hydroalkoxylation of ortho-Alkynylphenols: Scope and Mechanistic Insights
| Autor: | Lorena Alonso-Marañón, José Pérez Sestelo, Enrique Gómez-Bengoa, M. Montserrat Martínez, Luis A. Sarandeses |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
Nucleophilic addition 010405 organic chemistry Dimer Organic Chemistry Alkyne Regioselectivity 010402 general chemistry 01 natural sciences Medicinal chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Furan Intramolecular force Hydroalkoxylation |
| Zdroj: | The Journal of organic chemistry. 83(15) |
| ISSN: | 1520-6904 |
| Popis: | Indium(III) halides catalyze the hydroalkoxylation reaction of ortho-alkynylphenols to afford benzo[b]furans in good yields. The reaction proceeds with 5-endo-dig regioselectivity with a variety of phenols functionalized at the arene and alkyne moieties in high yields using InI3 (5 mol %) in DCE. Experimental and computational studies support a mechanism based on the indium(III) π-Lewis acid activation of the alkyne followed by nucleophilic addition of the phenol and final protodemetalation to afford the corresponding benzo[b]furan. DFT calculations suggest that dimer In2I6 is the catalytic species through a novel double coordination with the alkyne and the hydroxyl group. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|