Iron-Catalyzed C(sp3)-C(sp3) Bond Formation in 3,4-Dihydro-1,4-benzoxazin-2-ones

被引：13
作者：
Dong, Jie [1 ]
Min, Wenjian [1 ]
Li, Haitao [1 ]
Quan, Zhengjun [1 ]
Yang, Caixia [1 ]
Huo, Congde [1 ]
机构：
[1] Northwest Normal Univ, Coll Chem & Chem Engn, Lanzhou 730070, Gansu, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2017年 / 359卷 / 22期
基金：
中国国家自然科学基金;
关键词：
iron-catalyzed; carbon-carbon bond formation; one electron oxidation; benzoxazinone; dehydrogenative coupling; DEHYDROGENATIVE COUPLING REACTIONS; C-H FUNCTIONALIZATION; TRANSITION-METAL; VISIBLE-LIGHT; HETEROGENEOUS CATALYSIS; MOLECULAR-OXYGEN; GLYCINE DERIVATIVES; ORGANIC-SYNTHESIS; NANOPARTICLES; ELECTRON;
D O I：
10.1002/adsc.201700816
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A convenient iron-catalyzed oxidative dehydrogenative coupling reaction of 3,4-Dihydro-1,4-benzoxazin-2-ones with malonic esters or ketones was performed under mild reaction conditions to construct alkyl-alkyl C(sp(3))-C(sp(3)) bonds. This transformation can be catalyzed efficiently by magnetically recoverable iron nanoparticles and the catalyst can be recycled easily for 7 times without decreasing activity.
引用
收藏
页码：3940 / 3944
页数：5
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共 58 条
  • [41] Recent advances in transition-metal catalyzed reactions using molecular oxygen as the oxidant
    Shi, Zhuangzhi
    Zhang, Chun
    Tang, Conghui
    Jiao, Ning
    [J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (08) : 3381 - 3430
  • [42] Magnetically Separable Nanocatalysts: Bridges between Homogeneous and Heterogeneous Catalysis
    Shylesh, Sankaranarayanapillai
    Schuenemann, Volker
    Thiel, Werner R.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (20) : 3428 - 3459
  • [43] Superparamagnetic nanoparticle-supported catalysis of Suzuki cross-coupling reactions
    Stevens, PD
    Fan, JD
    Gardimalla, HMR
    Yen, M
    Gao, Y
    [J]. ORGANIC LETTERS, 2005, 7 (11) : 2085 - 2088
  • [44] The electron is a catalyst
    Studer, Armido
    Curran, Dennis P.
    [J]. NATURE CHEMISTRY, 2014, 6 (09) : 765 - 773
  • [45] Visible Light Mediated Cyclization of Tertiary Anilines with Maleimides Using Nickel(II) Oxide Surface-Modified Titanium Dioxide Catalyst
    Tang, Jian
    Grampp, Gunter
    Liu, Yun
    Wang, Bing-Xiang
    Tao, Fei-Fei
    Wang, Li-Jun
    Liang, Xue-Zheng
    Xiao, Hui-Quan
    Shen, Yong-Miao
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (05) : 2724 - 2732
  • [46] Efficient and General Aerobic Oxidative Cross-Coupling of THIQs with Organozinc Reagents Catalyzed by CuCl2: Proof of a Radical Intermediate
    Wang, Tongtong
    Schrempp, Michael
    Berndhaeuser, Andreas
    Schiemann, Olav
    Menche, Dirk
    [J]. ORGANIC LETTERS, 2015, 17 (16) : 3982 - 3985
  • [47] Cobalt-Catalyzed Cross-Dehydrogenative Coupling Reaction in Water by Visible Light
    Wu, Cheng-Juan
    Zhong, Jian-Ji
    Meng, Qing-Yuan
    Lei, Tao
    Gao, Xue-Wang
    Tung, Chen-Ho
    Wu, Li-Zhu
    [J]. ORGANIC LETTERS, 2015, 17 (04) : 884 - 887
  • [48] Cross-Dehydrogenative Coupling Reactions by Transition-Metal and Aminocatalysis for the Synthesis of Amino Acid Derivatives
    Xie, Jin
    Huang, Zhi-Zhen
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (52) : 10181 - 10185
  • [49] Copper-Catalyzed Aerobic Enantioselective Cross-Dehydrogenative Coupling of N-Aryl Glycine Esters with Terminal Alkynes
    Xie, Zhiyu
    Liu, Xigong
    Liu, Lei
    [J]. ORGANIC LETTERS, 2016, 18 (12) : 2982 - 2985
  • [50] Dual C-H functionalization of N-aryl tetrahydroisoquinolines: a highly diastereoselective synthesis of dibenzo[a,f]quinolizines via visible-light induced oxidation and inverse electron-demand aza-Diels-Alder reaction
    Xu, Guo-Qiang
    Li, Chen-Guang
    Liu, Ming-Qian
    Cao, Jian
    Luo, Yong-Chun
    Xu, Peng-Fei
    [J]. CHEMICAL COMMUNICATIONS, 2016, 52 (06) : 1190 - 1193
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