Copper-catalyzed synthesis of oxime ethers from iminoxy radical (C=N-O•) and maleimides via radical addition

被引：2
|
作者：
Han, Ziwei [1 ]
Shen, Subo [1 ]
Zheng, Feng [2 ]
Hu, Han [1 ]
Zhang, Jianmin [1 ,3 ]
Zhu, Shizheng [3 ]
机构：
[1] Shanghai Univ, Coll Sci, Dept Chem, Shanghai 200444, Peoples R China
[2] Shanghai Aerosp Chem Applicat Res Inst, Shanghai 201109, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
来源：
TETRAHEDRON LETTERS | 2019年 / 60卷 / 43期
关键词：
Copper-catalyzed; Radical addition; Oxime radical; Maleimides; ELECTRON-SPIN-RESONANCE; C-H FUNCTIONALIZATION; DERIVATIVES; BIOACTIVITY; OXIDATION; KETOXIMES; ANALOGS; DESIGN; AGENTS;
D O I：
10.1016/j.tetlet.2019.151188
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient Cu(II)-catalyzed radical addition of maleimides has been achieved. The identified copper catalyst enables the formation of oxime radicals (N-O-center dot) by cleaving the O-H bond in ketoximes, followed by the radical addition to N-substituted maleimides. The oxime radicals (N-O-center dot) were detected and confirmed by EPR spectroscopy and variable-temperature H-1 NMR. The simple one-pot reaction realizes the facile preparation of a variety of oxime ether adduct products in moderate to good yields. (C) 2019 Elsevier Ltd. All rights reserved.
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页数：5
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