Citation: Changwei Chen, Hongyu Zhang, Gang Xu, Sunliang Cui. Oxoarylation of ynamides with N-aryl hydroxamic acids[J]. Chinese Chemical Letters, ;2021, 32(8): 2551-2554. doi: 10.1016/j.cclet.2021.02.054 shu

Oxoarylation of ynamides with N-aryl hydroxamic acids

Changwei Chen ^b ,
Hongyu Zhang ^a ,
Gang Xu ^{a, *,} ,
Sunliang Cui ^b

a.
College of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, China
b.
College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, China

xugang_1030@zju.edu.cn

Received Date: 30 November 2020
Revised Date: 19 February 2021
Accepted Date: 22 February 2021
Available Online: 26 February 2021

Figures(5)

Ynamides are electron-rich alkynes with unique reactivities and act as flexible building blocks in organic synthesis. Therefore, the investigation for transformation of ynamides with exceptional selectivity and efficiency is attractive and interesting. Herein, we report an oxoarylation of ynamides with N-aryl hydroxamic acids. In the presence of catalytic Cu(OTf)₂, both the terminal and internal ynamides could undergo an addition/[3,3] sigmatropic rearrangement cascade with N-aryl hydroxamic acids to achieve oxoarylation, along with providing selective entry to (ortho-amino)arylacetamides and oxindoles. Moreover, deuterium-labelling reaction and gram-scale reaction were conducted to probe the mechanism and showcase the scalability.
- Ynamide,
- Hydroxamic acid,
- Oxoarylation,
- Oxindole,
- Rearrangement
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