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Chinese Journal of Organic Chemistry >

2019 , Vol. 39 >Issue 12: 3524 - 3531

DOI: https://doi.org/10.6023/cjoc201905006

Copper-Catalyzed Cyanoisopropylalkenylation of N-Alkenyl-acrylamides to Give 1,3-Dihydropyrrol-2-ones

  • Dai Enrui ,
  • Luo Qing ,
  • Chen Chunlin ,
  • Ying Fengyuan ,
  • Dong Ying ,
  • Liu Yingjie ,
  • Wang Baoling ,
  • Ma Yinhai ,
  • Liang Deqiang
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  • a Department of Chemistry, Kunming University, Kunming 650214;
    b College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan 250014;
    c Engineering Research Center for Medicine, Harbin University of Commerce College of Pharmacy, Harbin 150076;
    d Yunnan Engineering Technology Research Center for Plastic Films, Kunming 650214

Received date: 2019-05-05

  Revised date: 2019-07-02

  Online published: 2019-08-01

Supported by

Project supported by the National Natural Science Foundation of China (No. 21702083), the Yunnan Ten Thousand Talent Program for Young Top-Notch Talents, the Program for Innovative Research Team (in Science and Technology) in Universities of Yunnan Province, the Applied Basic Research Programs of Yunnan Science and Technology Department (Nos. 2018FD028, 2018FH001-002), the Excellent Youth Project of Heilongjiang Natural Science Foundation (No. UNPYSCT-2016181), the Scientific Research Funds of Yunnan Education Department (No. 2017ZDX048) and the Research Foundation for Introduced Talents of Kunming University (No. YJL19001).

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Abstract

A copper-catalyzed cyanoisopropylation/cyclization cascade of N-alkenylacrylamides is presented, providing a straightforward and chemoselective access to 1,3-dihydropyrrol-2-ones. In acrylamide-based radical cyclization, radical-trapping groups are mainly restricted to aryl, alkynyl or cyano group. But in this reaction, the enaminic double bond was used as an inbuilt radical trap, while the olefinic bond of the acrylamidyl moiety acted as the radical acceptor. Such chemoselectivity might be attributed to polarity matching.

Key words： enamide; alkene; azo compound; radical reaction; copper

Cite this article

Dai Enrui , Luo Qing , Chen Chunlin , Ying Fengyuan , Dong Ying , Liu Yingjie , Wang Baoling , Ma Yinhai , Liang Deqiang . Copper-Catalyzed Cyanoisopropylalkenylation of N-Alkenyl-acrylamides to Give 1,3-Dihydropyrrol-2-ones[J]. Chinese Journal of Organic Chemistry, 2019 , 39(12) : 3524 -3531 . DOI: 10.6023/cjoc201905006

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