Citation: Chong-Yang Shi, Jian-Xing Gong, Zhen Li, Chao Shu, Long-Wu Ye, Qing Sun, Bo Zhou, Xin-Qi Zhu. Gold-catalyzed intermolecular amination of allyl azides with ynamides: Efficient construction of 3-azabicyclo[3.1.0] scaffold[J]. Chinese Chemical Letters, ;2025, 36(2): 109895. doi: 10.1016/j.cclet.2024.109895 shu

Gold-catalyzed intermolecular amination of allyl azides with ynamides: Efficient construction of 3-azabicyclo[3.1.0] scaffold

Chong-Yang Shi ^a ,
Jian-Xing Gong ^a ,
Zhen Li ^a ,
Chao Shu ^b ,
Long-Wu Ye ^{a, b, c, *,} ,
Qing Sun ^{d, *,} ,
Bo Zhou ^b ,
Xin-Qi Zhu ^{a, *,}

a.
College of Chemistry and Chemical Engineering, Yunnan Normal University, Kunming 650500, China
b.
Key Laboratory of Chemical Biology of Fujian Province, State Key Laboratory of Physical Chemistry of Solid Surfaces, and College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China
c.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
d.
Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang 330063, China

longwuye@xmu.edu.cn

sunqing@nchu.edu.cn

xinqizhu@ynnu.edu.cn

Received Date: 31 January 2024
Revised Date: 8 April 2024
Accepted Date: 15 April 2024
Available Online: 16 April 2024

Figures(8)

Gold-catalyzed amination reactions based on azides via α-imino gold carbene intermediates have attracted extensive attention in the past decades because this methodology leads to the facile and efficient construction of synthetically useful N-containing molecules, especially valuable N-heterocycles. However, successful examples of intermolecular generation of α-imino gold carbenes by using azides as amination reagents are rarely explored probably due to the weak nucleophilicity of azides. Herein, we disclose an efficient gold-catalyzed intermolecular aminative cyclopropanation of ynamides with the allyl azides, enabling flexible synthesis of a wide range of valuable 3-azabicyclo[3.1.0]hex-2-ene derivatives in good to excellent yields with excellent diastereoselectivities. Importantly, this protocol represents the first use of allyl azide as an efficient amination reagent in gold-catalyzed alkyne amination reactions.
- Gold,
- Azides,
- Alkynes,
- Amination,
- Heterocycles
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沈阳化工大学材料科学与工程学院沈阳 110142