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Electricity-driven enantioselective cross-dehydrogenative coupling of two C(sp3)-H bonds enabled by organocatalysis
Chinese Chemical Letters ( IF 9.4 ) Pub Date : 2024-05-28 , DOI: 10.1016/j.cclet.2023.109445
Yuemin Chen , Yunqi Wu , Guoao Wang , Feihu Cui , Haitao Tang , Yingming Pan

An efficient and scalable electrochemical asymmetric protocol with metal-free catalysts and even without additional oxidants for the cross-dehydrogenative coupling reaction (CDC) of two C(sp)-H bonds is reported. A series of aldehydes including natural products and various substrates containing C(sp)-H bonds including xanthenes, acridines, cycloheptatrienes and even diarylmethane have been shown to undergo asymmetric CDC to afford a series of carbon-carbon bond coupling products with up to 94% yield and 98% . Mechanistic studies such as radical clock experiment suggest that the reaction proceeds nucleophilic attack by enamine under electrochemical conditions.

中文翻译:


有机催化下两个 C(sp3)-H 键的电驱动对映选择性交叉脱氢偶联



报道了一种高效且可扩展的电化学不对称方案,使用无金属催化剂,甚至无需额外的氧化剂,即可进行两个 C(sp)-H 键的交叉脱氢偶联反应 (CDC)。一系列醛,包括天然产物和各种含有 C(sp)-H 键的底物,包括呫吨、吖啶、环庚三烯甚至二芳基甲烷,已被证明经过不对称 CDC,可提供一系列碳-碳键偶联产物,其偶联率高达 94%产率98%。自由基时钟实验等机理研究表明,该反应在电化学条件下通过烯胺进行亲核攻击。
更新日期:2024-05-28
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