通过电化学与有机催化相结合实现四氢异喹啉的C(sp)-H烯基化反应
C(sp)-H Alkenylation of Tetrahydroisoquinolines via Merging Electrochemistry and Organocatalysis.
作者信息
Liu Hui-Lin, He Zeng, Wang Na-Na, Xu Hao, Fang Ping, Mei Tian-Sheng
机构信息
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P.R. China.
Key Laboratory of Pesticides & Chemical Biology Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P.R. China.
出版信息
Org Lett. 2023 Feb 3;25(4):608-613. doi: 10.1021/acs.orglett.2c04136. Epub 2023 Jan 25.
C(sp)-H alkenylation of tetrahydroisoquinoline by merging Shono oxidation and the Morita-Baylis-Hillman reaction is developed, employing 4-dimethylaminopyridine as an organocatalyst and TEMPO/NaBr as an electrocatalyst. The reaction proceeds via the interception of an iminium cation intermediate, which is generated in situ from anodic oxidation, leading to aza-Morita-Baylis-Hillman reaction products. Additionally, the use of TEMPO and NaBr as mediators is crucial to avoid the decomposition of products by lowering the oxidation potential of the reaction.
通过结合肖诺氧化反应和森田-贝利斯-希尔曼反应，开发了四氢异喹啉的C(sp)-H烯基化反应，使用4-二甲氨基吡啶作为有机催化剂，TEMPO/NaBr作为电催化剂。该反应通过捕获亚胺阳离子中间体进行，该中间体由阳极氧化原位生成，从而生成氮杂-森田-贝利斯-希尔曼反应产物。此外，使用TEMPO和NaBr作为介质对于通过降低反应的氧化电位来避免产物分解至关重要。
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