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Electrochemical Dimerization of Phenylpropenoids and the Surprising Antioxidant Activity of the Resultant Quinone Methide Dimers
Author(s) -
Romero Kevin J.,
Galliher Matthew S.,
Raycroft Mark A. R.,
Chauvin JeanPhilippe R.,
Bosque Irene,
Pratt Derek A.,
Stephenson Corey R. J.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201810870
Subject(s) - autoxidation , quinone methide , chemistry , radical , quinone , phenols , dimer , electrochemistry , quenching (fluorescence) , photochemistry , antioxidant , combinatorial chemistry , organic chemistry , electrode , physics , quantum mechanics , fluorescence
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.