Copper-catalyzed regioselective allylic oxidation of olefins via C-H activation

被引：20
|
作者：
Zhu, Nengbo [1 ]
Qian, Bo [1 ]
Xiong, Haigen [1 ]
Bao, Hongli [1 ]
机构：
[1] Univ Chinese Acad Sci, Fujian Inst Res Struct Matter, Key Lab Coal Ethylene Glycol & Its Related Techno, State Key Lab Struct Chem, 155 Yangqiao Rd West, Fuzhou 350002, Fujian, Peoples R China
来源：
TETRAHEDRON LETTERS | 2017年 / 58卷 / 43期
关键词：
Allylic oxidation; Olefin; Regioselective; Diacyl peroxides; Copper catalysis; Allylic radical; TERT-BUTYL PERBENZOATE; BOND FUNCTIONALIZATION; SUBSTITUTION-REACTIONS; ELECTRON-TRANSFER; PALLADIUM SALTS; COMPLEX; ALKENES; MECHANISM; ACETOXYLATION; PERESTERS;
D O I：
10.1016/j.tetlet.2017.09.047
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A regioselective oxidation of allylic C-H bond to C-O bond catalyzed by copper (I) was developed with diacyl peroxides as oxidants. The oxidation of allylic C-H bond was accomplished with good yield and regioselectivity under mild reaction conditions. This method has a broad substrate scope including cyclic olefins, terminal and internal acyclic olefins and allyl benzene compounds. The reaction proceeds by a radical mechanism as suggested by spin trapping experiments. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4125 / 4128
页数：4
相关论文
共 50 条
  • [1] Copper-catalyzed allylic C-H phosphonation
    Yang, Bin
    Zhang, Hong-Yu
    Yang, Shang-Dong
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (12) : 3561 - 3565
  • [2] Copper-Catalyzed Regioselective Cyanation of Indoles via C-H Bond Activation with a-Aminoacetonitriles
    Ahmad, Muhammad Siddique
    Qasim, Ruqiya
    Zeng, Bing
    Zhang, Qing
    Shah, Ehtesham Ul Haq
    Din, Nasar Ud
    Wang, Qifeng
    Meguellati, Kamel
    [J]. SYNTHESIS-STUTTGART, 2023, 55 (19): : 3145 - 3152
  • [3] Copper-catalyzed enantioselective allylic oxidation of acyclic olefins
    Zhang, Bo
    Zhu, Shou-Fei
    Zhou, Qi-Lin
    [J]. TETRAHEDRON LETTERS, 2013, 54 (21) : 2665 - 2668
  • [4] Copper-catalyzed amidation of allylic and benzylic C-H bonds
    Pelletier, Guillaume
    Powell, David A.
    [J]. ORGANIC LETTERS, 2006, 8 (26) : 6031 - 6034
  • [5] Copper-Catalyzed Trifluoromethylation of Terminal Alkenes through Allylic C-H Bond Activation
    Xu, Jun
    Fu, Yao
    Luo, Dong-Fen
    Jiang, Yuan-Ye
    Xiao, Bin
    Liu, Zhao-Jing
    Gong, Tian-Jun
    Liu, Lei
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (39) : 15300 - 15303
  • [6] Copper-Catalyzed Regioselective ortho C-H Cyanation of Vinylarenes
    Yang, Yang
    Buchwald, Stephen L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (33) : 8677 - 8681
  • [7] Copper-Catalyzed Regioselective C-H Iodination of Aromatic Carboxamides
    Wu, Chuanguang
    Zhou, Hui
    Wu, Qiaolin
    He, Mina
    Li, Pei
    Su, Qing
    Mu, Ying
    [J]. SYNLETT, 2016, 27 (06) : 868 - 875
  • [8] Copper-Catalyzed Regioselective Nitration and Azidation of 1-Naphthylamine Derivatives via Remote C-H Activation
    Dou, Yandong
    Yin, Biao
    Zhang, Pengfei
    Zhu, Qing
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (33) : 4571 - 4576
  • [9] Copper-catalyzed oxidative amidation of dibenzylamines via C-H bond activation
    Hu, Jinjin
    Zuo, Xiujin
    Huang, Hanmin
    [J]. CHINESE JOURNAL OF CATALYSIS, 2013, 34 (09) : 1644 - 1650
  • [10] Copper-Catalyzed Regioselective C-H Sulfonylation of 8-Aminoquinolines
    Wei, Jun
    Jiang, Jingxing
    Xiao, Xinsheng
    Lin, Dongen
    Deng, Yuanfu
    Ke, Zhuofeng
    Jiang, Huanfeng
    Zeng, Wei
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (03): : 946 - 955
12345