Zhu Fengxiang, Wu Huanan, Wu Xiao-Feng
School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, China.
Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China.
Org Lett. 2025 Jul 18;27(28):7714-7718. doi: 10.1021/acs.orglett.5c02491. Epub 2025 Jul 4.
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 stereocontrol, and broad functional group tolerance, while the retained C-Se bond offers versatility for downstream derivatization.
在此，我们报道了一种钯催化的烷氧羰基化策略，该策略能够从市售起始原料直接合成三取代硒代肉桂酸酯。该方法通过在单一催化操作中实现乙烯基硒化物的高效区域和立体选择性安装，解决了传统方法在构建空间拥挤的三取代衍生物方面的局限性。该方案建立了一个强大的平台，用于合成具有潜在应用于合成化学和药物化学的结构复杂的肉桂酸酯骨架。关键优势包括操作简单、克级规模可扩展性、高区域控制和立体控制以及广泛的官能团耐受性，同时保留的C-Se键为下游衍生化提供了多功能性。
