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Updated: Mar 18, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Direct conversion from alkenes to alkynes
Junhong Meng1,2,3, Yiqi Liang1,2,3, Ruilin Xu1,2,3
1State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing, China.
Abstract:
Alkynes are widely used as feedstock chemicals and functional groups in organic chemistry1,2. However, although the hydrogenation from an alkyne to an alkene is well established, typical methods for the reverse reaction-conversion of an alkene to an alkyne-are based on elimination chemistry reported in the 1860s3 and use forcing conditions (strong base or high temperatures)4-6. This precludes more general application on functional molecules. Here we report a recyclable selenanthrene reagent that mediates alkenes desaturation to alkynes under mild conditions. This method shows broad compatibility with both classical leaving groups and sensitive functional groups, enabling application late-stage in the efficient synthesis of complex alkynes. Moreover, this platform enables Z/E alkenes configuration inversion or sorting that are inaccessible with existing methods, highlighting its potential for diverse downstream derivatizations.
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