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Synthesis 2022; 54(14): 3262-3270
DOI: 10.1055/a-1804-8859
paper

Radical Oxyazidation of Alkenes in Pure Water

Jinfeng Cui
a   College of Chemistry, Fuzhou University, Fuzhou, Fujian 350108, P. R. of China
b   Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, P. R. of China
,
Huan Zhou∗
b   Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, P. R. of China
,
Yajun Li∗
b   Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, P. R. of China
,
Hongli Bao 
b   Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, P. R. of China
c   University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
› Author AffiliationsThis work was supported by the National Natural Science Foundation of China (NSFC) (22001251, 21871258, 21922112), the National Key Research and Development Program of China (2017YFA0700103), and the Strategic Priority Research Program of the Chinese Academy of Sciences (XDB20000000).
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Abstract

Compared to universal radical difunctionalizations of alkenes that are performed with organic solvents, such reactions with water as the sole solvent are rarely reported. Concerning the global consensus on environmental issues, we have developed herein a method for the radical oxyazidation of alkenes in pure water. This reaction allows the construction of C–N and C–O bonds in a one-pot process. Styrenes, 1,3-dienes, and unactivated alkenes react smoothly under mild and environmentally benign conditions to afford a wide scope of functionalized azides in excellent yields and selectivities.

Key words

radicals - oxyazidation - alkenes - water - TEMPO - copper

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1804-8859.
  • Supporting Information


Publication History

Received: 09 February 2022

Accepted after revision: 22 March 2022

Accepted Manuscript online:
22 March 2022

Article published online:
25 April 2022

© 2022. Thieme. All rights reserved

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