Citation: Shihaozhi Wang, Jia-Hui Shi, Shan Xu, Xue-Jing Zhang, Ming Yan. Palladium-catalyzed carbene C-H insertion reaction of non-activated arenes[J]. Chinese Chemical Letters, ;2026, 37(4): 111225. doi: 10.1016/j.cclet.2025.111225 shu

Palladium-catalyzed carbene C-H insertion reaction of non-activated arenes

State Key Laboratory of Anti-Infective Drug Discovery and Development, Guangdong Provincial Key Laboratory of Chiral Molecules and Drug Discovery, School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, China

zhangxj33@mail.sysu.edu.cn

yanming@mail.sysu.edu.cn

Received Date: 29 January 2025
Revised Date: 3 April 2025
Accepted Date: 16 April 2025
Available Online: 16 April 2025

Figures(5)

In this study, we report a palladium-catalyzed carbene C-H insertion reaction of non-activated arenes using N-tosylhydrazones as both carbene and olefin precursors. This method consists of a two-step, one-pot process, where the arenes are first thianthrenated and then undergo migratory insertion/β-H elimination with N-tosylhydrazones to form aryl alkenes. This highly site-selective C-H alkenylation of arenes demonstrates a relatively broad substrate scope and exhibits high tolerance for halogen substituents. Importantly, this transformation allows for the modification of the arene moiety in commercially available bioactive molecules, underscoring its significant potential for late-stage functionalization of arene-containing pharmaceuticals.
- Carbene C-H insertion,
- Thianthrenation,
- Non-activated arenes,
- N-Tosylhydrazone,
- Palladium catalysis
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