Dual Catalysis Relay: Coupling of Aldehydes and Alkenes Enabled by Visible-Light and NHC-Catalyzed Cross-Double C-H Functionalizations
Dual Catalysis Relay: Coupling of Aldehydes and Alkenes Enabled by Visible-Light and NHC-Catalyzed Cross-Double C-H Functionalizations
复制标题
双催化中继：可见光和 NHC 催化交叉双 C-H 官能化实现醛和烯烃的偶联
DOI：
10.1021/acscatal.1c02890
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发表时间：
2021
期刊：
影响因子：
12.9
通讯作者：
Shu Wei
中科院分区：
文献类型：
--
作者：
Liu Ming-Shang;Min Lin;Chen Bi-Hong;Shu Wei
两个不同的惰性C-H键的直接官能化是构建C-C键的最理想的方法。在此，我们报告了一个分子间乙烯化的醛使用烯烃作为乙烯化试剂，通过连续的两重C-H官能化。可见光和N-杂环卡宾催化的合并允许烯烃与醛通过双催化中继实现的交叉偶联机制偶联。联苯醌的使用对于该反应的成功是必不可少的，联苯醌在反应中起着有趣的双重作用，作为电子受体以及自由基库，用于使C-C形成过程能够进行自由基偶联。
Direct functionalizations of two distinct inert C–H bonds represent the most ideal ways to construct C–C bonds. Herein, we report an intermolecular vinylation of aldehydes using alkenes as the vinylating reagents through sequential two-fold C–H functionalizations. The merging of visible light and N-heterocyclic carbene catalysis allows for the coupling of alkenes with aldehydes through a dual catalysis relay enabled cross-dehydrogenative coupling mechanism. The use of diphenoquinone is essential for the success of this reaction, which plays an intriguing two-fold role in the reaction, as an electron acceptor as well as a radical reservoir for the radical coupling enabling the C–C forming process.