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Published on: September 8, 2013
Palladium-Catalyzed Selenylative Alkoxycarbonylation of Alkynes toward β-Selenated Cinnamic Acid Esters
Fengxiang Zhu1, Huanan Wu1, Xiao-Feng Wu2,3
1School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, China.
Abstract:
Herein, we report a palladium-catalyzed alkoxycarbonylation strategy enabling the direct synthesis of trisubstituted selenated cinnamate esters from commercially available starting materials. This method addresses the limitations of conventional approaches in constructing sterically congested trisubstituted derivatives by achieving efficient regio- and stereoselective installation of vinyl selenides in a single catalytic operation. The protocol establishes a robust platform for synthesizing architecturally complex cinnamate frameworks with potential applications in synthetic and medicinal chemistry. Key advantages include operational simplicity, gram-scale scalability, high regiocontrol and Z stereocontrol, and broad functional group tolerance, while the retained C-Se bond offers versatility for downstream derivatization.
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