Citation: Wang Guodong, Guo Yanhui, Wan Jieping. Base-Promoted, Metal- and Oxidant-Free C=C Bond Cleavage in Enaminones for Ambient Synthesis of NH₂-Amidines[J]. Chinese Journal of Organic Chemistry, ;2020, 40(3): 645-650. doi: 10.6023/cjoc201912018 shu

Base-Promoted, Metal- and Oxidant-Free C=C Bond Cleavage in Enaminones for Ambient Synthesis of NH₂-Amidines

College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022

Corresponding author: Wan Jieping, wanjieping@jxnu.edu.cn
Received Date: 12 December 2019
Revised Date: 16 December 2019
Available Online: 19 December 2019
Fund Project: the National Natural Science Foundation of China 21562025Project supported by the National Natural Science Foundation of China (No. 21562025)

Figures(1)

The C=C double bond cleavage of NH₂-functionalized enaminones has been realized at room temperature to provide various N-sulfonyl amidines by reacting with sulfonyl azides. The reactions take place with good substrate tolerance in the presence of 1, 8-Diazabicyclo[5.4.0]undec-7-ene (DBU) without any metal or oxidant reagent. The ¹⁵N-labelling experiment on enaminone indicates that the sulfonyl azide component donates solely the sulfonamide fragment, and the reaction mechanism involving a key decomposition of the in situ generated 1, 2, 3-triazoline intermediate is convictively supported.
- Enaminone,
- C=C bond cleavage,
- Metal-free,
- Oxidant-free,
- Amidines
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Base-Promoted, Metal- and Oxidant-Free C=C Bond Cleavage in Enaminones for Ambient Synthesis of NH2-Amidines

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通讯作者: 陈斌, bchen63@163.com

Base-Promoted, Metal- and Oxidant-Free C=C Bond Cleavage in Enaminones for Ambient Synthesis of NH₂-Amidines