Citation: Haoran Shi, Jiaxin Wang, Yuqin Zhu, Hongyang Li, Guodong Ju, Lanlan Zhang, Chao Wang. Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis[J]. Chinese Chemical Letters, ;2024, 35(7): 109333. doi: 10.1016/j.cclet.2023.109333 shu

Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis

Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, China

gdju@tjnu.edu.cn

chwang@tjnu.edu.cn

Received Date: 9 September 2023
Revised Date: 6 November 2023
Accepted Date: 16 November 2023
Available Online: 23 November 2023

Figures(4)

Herein, we report the migratory hydroarylation of unactivated alkenes with aryl iodides using native and weakly coordinating amide directors under mild conditions. Synergistic coordination of the monodentate directing group and the ligand enable the highly regioselective migratory hydroarylation via a chain walking process to form the thermodynamically stable five-membered nickelacyle intermediate. The protocol provides a variety of valuable α-aryl-substituted alkylamine products, and exhibited good functional group tolerance. The modification of bioactive compounds such as fenofibrate and indomethacin further highlights the synthetic value of this protocol.
- Alkenes,
- Hydroarylation,
- Chain-walking,
- Regioselective,
- Nickel catalysis
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沈阳化工大学材料科学与工程学院沈阳 110142

Highly selective α-C(sp3)-H arylation of alkenyl amides via nickel chain-walking catalysis

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Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis