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Synlett 2018; 29(12): 1664-1668
DOI: 10.1055/s-0037-1609752
letter
© Georg Thieme Verlag Stuttgart · New York

Room Temperature, Metal-Free, Radical Chloroazidation of 1,6-Enynes

Wei-Wei Ying
School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China   Email: weiwenting@nbu.edu.cn
,
Wei-Ting Chen
School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China   Email: weiwenting@nbu.edu.cn
,
Wen-Hui Bao
School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China   Email: weiwenting@nbu.edu.cn
,
Le-Han Gao
School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China   Email: weiwenting@nbu.edu.cn
,
Xin-Ye Wang
School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China   Email: weiwenting@nbu.edu.cn
,
Gan-Ping Chen
School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China   Email: weiwenting@nbu.edu.cn
,
Guo-Ping Ge
School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China   Email: weiwenting@nbu.edu.cn
,
Wen-Ting Wei*
School of Materials Science and Chemical Engineering, Ningbo University, Ningbo 315211, P. R. of China   Email: weiwenting@nbu.edu.cn
› Author AffiliationsThis research is sponsored by the Natural Science Foundation of Zhejiang Province (No. LQ18B020002), State Key Laboratory of Analytical Chemistry for Life Science (No. SKLACLS1804), the Open Subject of State Key Laboratory of Chemo/Biosensing and Chemometrics (2017016), Education Foundation of Zhejiang Province (No. Y201737123), Research Funds of NBU (No. ZX2016000706), Foundation of Ningbo University (No. XYL17009), and the K. C. Wong Magna Fund in Ningbo University. Dr. G.-P. Ge also thank the Ningbo Municipal Natural Science Foundation (No. 2016A610052).
Further Information

Publication History

Received: 14 February 2018

Accepted after revision: 15 April 2018

Publication Date:
17 May 2018 (online)

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Abstract

Without employing any transition metal, a mild, practical, and environmentally attractive methodology has been developed for the chloroazidation of 1,6-enynes at room temperature. In this radical cascade process, three new chemical bonds, including C–Cl (Br, I), C–N, and C–C bonds, are formed in one step for the construction of 2-pyrrolidinones. The method is valuable because of its mild reaction conditions, operational simplicity, and the rich biological activity of the corresponding 2-pyrrolidinone products.

Key words

room-temperature reactions - metal-free reactions - radicals - cascade processes

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609752.
  • Supporting Information
 

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