C(sp3)-H Alkenylation of Tetrahydroisoquinolines via Merging Electrochemistry and Organocatalysis

作者：Liu, Hui -Lin; He, Zeng; Wang, Na-Na; Xu, Hao^*; Fang, Ping^*; Mei, Tian-Sheng^*

来源：Organic Letters, 2023, 25(4): 608-613.

DOI：10.1021/acs.orglett.2c04136

• C-H FUNCTIONALIZATION
• BAYLIS-HILLMAN REACTION
• TERTIARY-AMINES
• OXIDATION
• ELECTROSYNTHESIS
• CHEMISTRY
• OLEFINATION
• PHOTOREDOX
• CATALYSIS
• BONDS

C(sp(3))-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.

• 单位
  中国科学院; 中国科学院研究生院