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Published on: November 15, 2017
Access to (Z)-1,2-Dicyanoethylenes via Desulfurization of 2,5-Dinitrothiophene
Song-Hua Li1, Xue-Ning Li1, Sheng-Nan Liu1
1School of Chemical Sciences, University of Chinese Academy of Sciences, Beijing 101408, China.
Abstract:
We report herein a thiophene-desulfurization-enabled strategy for the stereoselective synthesis of (Z)-1,2-dicyanoethylenes [(Z)-1,2-DCEs] from 2,5-dinitrothiophenes as masked (Z)-1,2-DCE synthons. The reaction proceeds through sequential PPh3-mediated deoxygenation and desulfurization, with the generated Ph3P═O byproduct recycled by a PhSiH3/TfOH reduction system. This protocol exhibits broad substrate scope and high to exclusive Z selectivity, providing an efficient platform for accessing structurally diverse (Z)-1,2-DCEs with potential applications in organic synthesis and optoelectronic materials.
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