Iron-Catalyzed Transfer Hydrogenation in Aged N-Methyl-2-pyrrolidone: Reductive Ring-Opening of 3,5-Disubstituted Isoxazoles and Isoxazolines
| Autor: | William H. Hersh, Pak-Hing Leung, Xiaochen Liu, Netanel G Sapir, Wen Yang, Yu Chen, Dingqiao Yang, Dongsub Hong |
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| Rok vydání: | 2019 |
| Předmět: |
Hydrogen
010405 organic chemistry Reducing agent Iron catalyzed Organic Chemistry chemistry.chemical_element 010402 general chemistry Ring (chemistry) Transfer hydrogenation 01 natural sciences Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound chemistry N-Methyl-2-pyrrolidone Iron catalyst |
| Zdroj: | The Journal of Organic Chemistry. 84:16204-16213 |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | 3,5-Disubstituted isoxazoles and isoxazolines undergo an iron-catalyzed reductive ring-opening in aged N-methyl-2-pyrrolidone (NMP). 5-Hydroxy-N-methyl-2-pyrrolidone generated in situ via a simple activation of commercial NMP acts as the hydrogen donor in the iron-catalyzed transfer hydrogenation reaction. It is the first example employing a combination of an iron catalyst and 5-hydroxy-N-methyl-2-pyrrolidone as reducing agents in a transfer hydrogenation reaction. The protocol is highly efficient for the synthesis of β-enaminones and 1,3-diketones, providing a versatile route for the preparation of these 1,3-difunctional compounds bearing diversified substitution patterns. |
| Databáze: | OpenAIRE |
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