Electrochemical Dimerization of Phenylpropenoids and the Surprising Antioxidant Activity of the Resultant Quinone Methide Dimers
| Autor: | Corey R. J. Stephenson, Irene Bosque, Kevin J Romero, Derek A. Pratt, Matthew S. Galliher, Jean-Philippe R. Chauvin, Mark A. R. Raycroft |
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| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
Antioxidant
medicine.medical_treatment Dimer Electrochemistry 010402 general chemistry 01 natural sciences Catalysis Article Antioxidants chemistry.chemical_compound medicine Phenols Indolequinones Autoxidation Molecular Structure Phenylpropionates 010405 organic chemistry General Chemistry General Medicine Electrochemical Techniques Combinatorial chemistry Quinone methide 0104 chemical sciences chemistry Functional group Peroxyl radicals Dimerization |
| Popis: | A simple method for the dimerization of phenylpropenoid derivatives is reported. It leverages electrochemical oxidation of p-unsaturated phenols to access the dimeric materials in a biomimetic fashion. The mild nature of the transformation provides excellent functional group tolerance, resulting in a unified approach for the synthesis of a range of natural products and related analogues with excellent regiocontrol. The operational simplicity of the method allows for greater efficiency in the synthesis of complex natural products. Interestingly, the quinone methide dimer intermediates are potent radical-trapping antioxidants; more so than the phenols from which they are derived – or transformed to – despite the fact that they do not possess a labile H-atom for transfer to the peroxyl radicals that propagate autoxidation. |
| Databáze: | OpenAIRE |
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