Tetrahydropyranyl protection and deprotection of alcohols using a niobium-based Brønsted acid catalyst
| Autor: | Juan C. Scaiano, José Carlos Netto-Ferreira, Stefania Impellizzeri, Filipe Matos Lima, Charles-Oneil L. Crites, Geniece L. Hallett-Tapley, M. Luisa Marin |
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| Rok vydání: | 2016 |
| Předmět: |
Steric effects
010405 organic chemistry Chemistry Organic Chemistry General Chemistry 010402 general chemistry Heterogeneous catalysis 01 natural sciences Catalysis 0104 chemical sciences chemistry.chemical_compound Moiety Niobium oxide Phenol Organic chemistry Brønsted–Lowry acid–base theory Phosphoric acid |
| Zdroj: | Canadian Journal of Chemistry. 94:712-714 |
| ISSN: | 1480-3291 0008-4042 |
| DOI: | 10.1139/cjc-2015-0538 |
| Popis: | Solid niobium oxide treated with phosphoric acid (NbP) was used as a heterogeneous catalyst in the protection of a series of aliphatic alcohols as tetrahydropyranyl (THP) derivatives. Protection of primary alcohols using this material with strong Brønsted acid sites was achieved in good yields (75%–94%), while moderate values were obtained in the protection of secondary and tertiary alcohols (50%–84%), largely dependent on the steric hindrance in the proximity of the hydroxyl moiety. NbP also catalyzed deprotection of THP ethers derived from primary alcohols and phenol with moderate yields (65%–99%). |
| Databáze: | OpenAIRE |
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