New domino radical synthesis of aminoalcohols promoted by TiCl4–Zn/t-BuOOH system: selective hydroxyalkylation of amines in alcohol or in cyclic ether cosolvents
| Autor: | Angelo Clerici, Nadia Pastori, Carlo Punta, Simona Prosperini, Alessandra Ghilardi |
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| Rok vydání: | 2011 |
| Předmět: |
Titanium
Alkylation Free Radicals Chemistry Organic Chemistry Alcohol Biochemistry Domino Substrate Specificity Catalysis Zinc chemistry.chemical_compound tert-Butylhydroperoxide Ethers Cyclic Alcohols Cyclic ether Solvents Molecule Organic chemistry Amine gas treating Amines Physical and Theoretical Chemistry |
| Zdroj: | Organic & Biomolecular Chemistry. 9:3759 |
| ISSN: | 1477-0539 1477-0520 |
| DOI: | 10.1039/c1ob05191a |
| Popis: | We report a new and fast domino synthesis of aminoalcohols under mild conditions. The free-radical reaction of aliphatic and aromatic amines with alcohol cosolvents is promoted by means of the TiCl(4)-Zn/t-BuOOH system. According to the proposed mechanism, the amine reacts with two molecules of alcohol in an electrophilic-nucleophilic cascade process. This procedure, if compared with the TiCl(3)/t-BuOOH-mediated protocol previously reported, appears to be more selective, of more general applicability and affords the desired products in higher yields. Besides, with the same catalytic system it was possible to promote the reaction of primary arylamines with two molecules of cyclic ether, leading to the formation of a wider range of functionalized aminoalcohols. |
| Databáze: | OpenAIRE |
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