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Updated: Jan 15, 2026
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Electroreductive 1,4-Hydro(deutero)arylation of 1,3-Enynes Enabled by Terephthalonitrile: Entry to Trisubstituted
Boxiong Yang1, Ming Hu1, Chao Hu1
1State Key Laboratory of Advanced Optical Polymer and Manufacturing Technology, Qingdao Key Laboratory of Biomacromolecular Drug Discovery and Development, College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, China.
Abstract:
An electroreduction method for regioselective 1,4-hydro(deutero)arylation of 1,3-enynes with aryl iodides and H2O or D2O has been developed, delivering diverse aryl-functionalized trisubstituted allenes under mild, transition-metal-free, and external reductant-free conditions. Upon the activation of terephthalonitrile as the organic electron transfer mediator, the protocol enables the formation of aryl radicals via single-electron transfer (SET) reduction with aryl iodides. The protocol shows a broad substrate scope with a good functional group compatibility and allows deuterium labeling using D2O with up to 99% D-incorporation. Mechanistic studies support a cathodic radical anion-single electron reduction-cathodic radical polar crossover relay pathway, offering a sustainable approach to access trisubstituted allenes.
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