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
  • [31] Copper-catalyzed electrochemical C-H fluorination
    Hintz, Heather
    Bower, Jamey
    Tang, Jinghua
    LaLama, Matthew
    Sevov, Christo
    Zhang, Shiyu
    [J]. CHEM CATALYSIS, 2023, 3 (01):
  • [32] Copper-Catalyzed C-H Alkoxylation of Azoles
    Takemura, Noriaki
    Kuninobu, Yoichiro
    Kanai, Motomu
    [J]. ORGANIC LETTERS, 2013, 15 (04) : 844 - 847
  • [33] Copper-Catalyzed Intramolecular C-H Amination
    Barman, Dipti N.
    Nicholas, Kenneth M.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (05) : 908 - 911
  • [34] Copper-catalyzed C-H ethoxycarbonyldifluoromethylation of imidazoheterocycles
    Mishra, Subhajit
    Mondal, Pallab
    Ghosh, Monoranjan
    Mondal, Susmita
    Hajra, Alakananda
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (04) : 1432 - 1436
  • [35] Copper-Catalyzed Regioselective Allylic Cyanation of Allylic Compounds with Trimethylsilyl Cyanide
    Munemori, Daisuke
    Tsuji, Hiroaki
    Uchida, Kenta
    Suzuki, Tomoaki
    Isa, Kazuki
    Minakawa, Maki
    Kawatsura, Motoi
    [J]. SYNTHESIS-STUTTGART, 2014, 46 (20): : 2747 - 2750
  • [36] Copper-catalyzed synthesis of indolyl diketones via C-H oxidation/diacylation of indoles with arylglyoxal hydrates
    Wang, Cuiping
    Zhang, Zhiqiang
    Liu, Kui
    Yan, Jingbo
    Zhang, Tiexin
    Lu, Gonghao
    Meng, Qingtao
    Chi, Haijun
    Duan, Chunying
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (29) : 6185 - 6193
  • [37] Copper Catalyzed C-H Activation
    Kantam, M. Lakshmi
    Gadipelly, Chandrakanth
    Deshmukh, Gunjan
    Reddy, K. Rajender
    Bhargava, Suresh
    [J]. CHEMICAL RECORD, 2019, 19 (07): : 1302 - 1318
  • [38] Dearomatization of Indoles via Palladium-Catalyzed Allylic C-H Activation
    Zhang, Heng
    Hu, Rong-Bin
    Liu, Na
    Li, Shi-Xia
    Yang, Shang-Dong
    [J]. ORGANIC LETTERS, 2016, 18 (01) : 28 - 31
  • [39] Copper-catalyzed oxaziridine-mediated intramolecular C-H bond oxidation
    Motiwala, Hashim F.
    Gulgeze, Belgin
    Aube, Jeffrey
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [40] Copper-catalyzed one-pot oxidative amidation of alcohol to amide via C-H activation
    Gu, Jiajia
    Fang, Zheng
    Yang, Yuhang
    Yang, Zhao
    Wan, Li
    Li, Xin
    Wei, Ping
    Guo, Kai
    [J]. RSC ADVANCES, 2016, 6 (92) : 89413 - 89416
12345