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Electrochemical stereoselective synthesis of polysubstituted 1,4-dicarbonyl Z -alkenes via three-component coupling of sulfoxonium ylides and alkynes with water.

Hao-Ran LiYi-An RanYu-Yi ZhuWeisi GuoShao-Fei NiLi-Rong WenMing LiLin-Bao Zhang
Published in: Chemical science (2024)
The first straightforward strategy for the synthesis of 1,4-dicarbonyl Z -alkenes has been developed via an electrochemical cross-coupling reaction of sulfoxonium ylides and alkynes with water. The metal-free protocol showed an easy-to-handle nature, good functional group tolerance, and high Z -stereoselectivity, which is rare in previous cases. The proposed reaction mechanism was convincingly established by carrying out a series of control experiments, cyclic voltammetry experiments, and density functional theory (DFT) studies.
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