Citation: Yingying Shan, Lei Su, Dianpeng Chen, Min Yang, Wenlin Xie, Guanyinsheng Qiu. Palladium-catalyzed concerted [4 + 1] cyclization of prop-2-yn-1-ones and isocyanides[J]. Chinese Chemical Letters, ;2021, 32(1): 437-440. doi: 10.1016/j.cclet.2020.04.041 shu

Palladium-catalyzed concerted [4 + 1] cyclization of prop-2-yn-1-ones and isocyanides

Yingying Shan ^a ,
Lei Su ^a ,
Dianpeng Chen ^{a, *} ,
Min Yang ^b ,
Wenlin Xie ^c ,
Guanyinsheng Qiu ^{d, *}

a.
Chemistry and Chemical Engineering, Qufu Normal University, Qufu 273165, China
b.
Department of Forensic Science, Gannan Medical University, Ganzhou 341000, China
c.
School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China
d.
College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001, China

chendp@zju.edu.cn

qiuguanyinsheng@mail.zjxu.edu.cn

Received Date: 10 March 2020
Revised Date: 11 April 2020
Accepted Date: 23 April 2020
Available Online: 13 May 2020

Figures(5)

A palladium-catalyzed [4 + 1] cycloaddition of prop-2-yn-1-ones with double isocyanides is developed herein. The transformation worked well to produce a series of 2-amino-4-cyanofurans with high efficiency and a broad reaction scope. Based on mechanism studies, it is believed that the palladium-catalyzed [4 + 1] imidoylative cycloaddition of prop-2-yn-1-ones was concerted. Treated with aryl amine and H₂O, the [4 + 1] cycloaddition of prop-2-yn-1-ones with double isocyanides provided 2-amino-4-amidylpyrroles efficiently.
- [4 + 1] Cycloaddition,
- Isocyanides,
- Palladium catalysis,
- Furan,
- Pyrrole
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