Citation: Cong Tiantian, Wang Huamin, Liu Yuanyuan, Wu Haihong, Zhang Junliang. Phosphine-Mediated Sequential Staudinger/Aza-Michael Addition of Azides with Unsaturated Ketones to Synthesize β-Amino Substituted Ketones[J]. Chinese Journal of Organic Chemistry, ;2019, 39(8): 2157-2165. doi: 10.6023/cjoc201906005 shu

Phosphine-Mediated Sequential Staudinger/Aza-Michael Addition of Azides with Unsaturated Ketones to Synthesize β-Amino Substituted Ketones

a.
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062
b.
Department of Chemistry, Fudan University, Shanghai 200438

Corresponding author: Liu Yuanyuan, yyliu@chem.ecnu.edu.cn Wu Haihong, hhwu@chem.ecnu.edu.cn Zhang Junliang, junliangzhang@fudan.edu.cn
Received Date: 6 June 2019
Revised Date: 9 July 2019
Available Online: 17 August 2019
Fund Project: the Chenguang Program supported by Shanghai Education Development Foundation and Shanghai Municipal Education Commission 16CG22the Fundamental Research Funds for the Central Universities 21871088Project supported by the National Natural Science Foundation of China (No. 21871088), the Chenguang Program supported by Shanghai Education Development Foundation and Shanghai Municipal Education Commission (No. 16CG22), and the Fundamental Research Funds for the Central Universities (No. 21871088)Project supported by the National Natural Science Foundation of China 21871088

Figures(5)

A phosphine-mediated Staudinger/Aza-Michael addition of azides with trifluoromethyl substituted α, β-unsaturated ketones was developed, giving hydroamination products in medium to good yields (up to 96%). The hydroamination products could be prepared on gram scale and a wide range of substrates are tolerated under the optimized reaction conditions (30 examples). ³¹P NMR experiments indicate that this reaction was initiated by Staudinger reaction of azide with phosphine.
- phosphines,
- Staudinger reaction,
- aza-Michael addition,
- azides,
- hydroamination,
- alkenes
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