Citation: Liangfeng Yang, Liang Zeng, Yanping Zhu, Qiuan Wang, Jinheng Li. Copper-catalyzed photoredox 1,4-amidocyanation of 1,3-enynes with N-amidopyridin-1-ium salts and TMSCN: Facile access to α-amido allenyl nitriles[J]. Chinese Chemical Letters, ;2024, 35(11): 109685. doi: 10.1016/j.cclet.2024.109685 shu

Copper-catalyzed photoredox 1,4-amidocyanation of 1,3-enynes with N-amidopyridin-1-ium salts and TMSCN: Facile access to α-amido allenyl nitriles

Liangfeng Yang ^{a, b} ,
Liang Zeng ^{a, b} ,
Yanping Zhu ^{c, *,} ,
Qiuan Wang ^{a, *,} ,
Jinheng Li ^{a, b, c, d, *,}

a.
State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, China
b.
State Key Laboratory Base of Eco-Chemical Engineering, College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, China
c.
School of Pharmacy, Key Laboratory of Molecular Pharmacology and Drug Evaluation, Ministry of Education, Collaborative Innovation Center of Advanced Drug Delivery System and Biotech Drugs in Universities of Shandong, Yantai University, Yantai 264005, China
d.
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China

chemzyp@foxmail.com

wangqa@hnu.edu.cn

jhli@hnu.edu.cn

Received Date: 21 December 2023
Revised Date: 20 February 2024
Accepted Date: 27 February 2024
Available Online: 1 March 2024

Figures(4)

A new 1,4-amidocyanation of 1,3-enynes with N-amidopyridin-1-ium salts and TMSCN using a copper and photoredox synergetic catalysis for producing α-amido allenyl nitriles is developed. Employing N-amidopyridin-1-ium salts as the amidyl radical precursors, the reaction enables the formation of two new bonds, one C(sp³)-N bond and one C(sp²)-C(sp) bond, in a single reaction step. This reaction represents a mild, general route to the construction of the α-amido allenyl nitrile architectures, which characterizes a broad scope, a good functional group compatibility and an excellent selectivity.
- Copper,
- Photoredox catalysis,
- Amidocyanation,
- N-(Sulfonamido)pyridin-1-ium salts,
- 1,3-Enynes,
- α-Sulfonamido allenyl nitriles
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