Citation: Xiaoya Zhuo, Xiangwen Tan, Yi Wang, Wanqing Wu, Huanfeng Jiang. Palladium catalyzed tandem Heck/Tsuji-Trost and 6-endo cyclization reactions of aryl iodides, vinylacetic acid, and aryl amines[J]. Chinese Chemical Letters, ;2026, 37(6): 111777. doi: 10.1016/j.cclet.2025.111777 shu

Palladium catalyzed tandem Heck/Tsuji-Trost and 6-endo cyclization reactions of aryl iodides, vinylacetic acid, and aryl amines

Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510641, China

cewuwq@scut.edu.cn

jianghf@scut.edu.cn

Received Date: 23 April 2025
Revised Date: 14 August 2025
Accepted Date: 30 August 2025
Available Online: 2 September 2025

Figures(5)

Heck/Tsuji-Trost reaction and cyclization reactions have been established as efficient and practical strategies for constructing nitrogen-containing heterocyclic compounds. However, it is challenging to achieve a direct cascade of Heck/Tsuji-Trost and 6-endo cyclization reactions in one-pot synthesis, primarily due to the reactivity of intermediates and the regioselectivity control of the reaction. In this work, a palladium-catalyzed, Heck/Tsuji-Trost and 6-endo cyclization tandem reaction of aryl iodides, vinylacetic acid, and aryl amines has been developed, providing an effective approach for one-pot synthesis of substituted quinolines in moderate to good yields. The broad functional group tolerance, high regioselectivity, gram-scale experiments, and successful late-stage modification of natural products and pharmaceuticals proved the versatility and practicality of this method. Additionally, mechanistic experiments demonstrate that the branched amination product serves as a key intermediate in this reaction.
- Palladium catalyzed,
- Tandem reaction,
- Heck reaction,
- Tsuji-Trost reaction,
- 6-endo cyclization reaction
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