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Chinese Journal of Organic Chemistry >

2019 , Vol. 39 >Issue 8: 2157 - 2165

DOI: https://doi.org/10.6023/cjoc201906005

Articles

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

  • Cong Tiantian ,
  • Wang Huamin ,
  • Liu Yuanyuan ,
  • Wu Haihong ,
  • Zhang Junliang
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  • 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

Received date: 2019-06-06

  Revised date: 2019-07-09

  Online published: 2019-07-17

Supported by

Project 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).

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Abstract

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.

Key words： phosphines; Staudinger reaction; aza-Michael addition; azides; hydroamination; alkenes

Cite this article

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

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