Copper-Mediated Oxidative Functionalization of C(sp3)-H Bonds with Isoquinolines: Two-Step Synthesis of 5-Oxaprotoberberinones

被引:2
|
作者
Wang, Dingyi [1 ]
Zhang, Rongxing [1 ]
Deng, Ruihong [1 ]
Lin, Sen [1 ]
Guo, Shengmei [1 ]
Yan, Zhaohua [1 ]
机构
[1] Nanchang Univ, Coll Chem, Nanchang 330031, Jiangxi, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H AMINATION; EFFICIENT SYNTHESIS; METAL-FREE; AMIDATION; HYDROCARBONS; CYCLIZATION; ROSETTACIN; ACTIVATION; ANNULATION; ALKALOIDS;
D O I
10.1021/acs.joc.6b02145
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A copper-mediated oxidative functionalization of C(sp(3))-H bonds with isoquinolines via a radical process without ligands was achieved. The present system exhibits a novel pathway for the preparation of N-alkyl (benzyl) isoquinolin-1(2H)-ones in moderate to high yields. In addition, this procedure provides a simple method to afford 5-oxaprotoberberinones and their derivatives in two steps.
引用
收藏
页码:11162 / 11167
页数:6
相关论文
共 50 条
  • [21] Manganese(III) acetate catalyzed oxidative amination of benzylic C(sp3)-H bonds with nitriles
    Zhang, Yaxing
    Dong, Jianyu
    Liu, Lixin
    Liu, Long
    Zhou, Yongbo
    Yin, Shuang-Feng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (14) : 2897 - 2901
  • [22] Copper-catalyzed intermolecular C(sp3)-H bond functionalization towards the synthesis of tertiary carbamates
    Chikkade, Prasanna Kumara
    Kuninobu, Yoichiro
    Kanai, Motomu
    CHEMICAL SCIENCE, 2015, 6 (05) : 3195 - 3200
  • [23] Iodine-Mediated C-H Functionalization of sp, sp2, and sp3 Carbon: A Unified Multisubstrate Domino Approach for Isatin Synthesis
    Satish, Gandhesiri
    Polu, Ashok
    Ramar, Thangeswaran
    Ilangovan, Andivelu
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (10) : 5167 - 5175
  • [24] Iodine-Catalyzed Oxidative Functionalization of Azaarenes with Benzylic C(sp3)-H Bonds via N-Alkylation/Amidation Cascade: Two-Step Synthesis of Isoindolo[2,1-b]isoquinolin-7(5H)-one
    Luo, Wen-Kun
    Shi, Xin
    Zhou, Wang
    Yang, Luo
    ORGANIC LETTERS, 2016, 18 (09) : 2036 - 2039
  • [25] Selective functionalization of benzylic C(sp3)-H bonds to synthesize complex molecules
    Zhang, Yu
    Zhang, Tong
    Das, Shoubhik
    CHEM, 2022, 8 (12): : 3175 - 3201
  • [26] Visible light photocatalysis in chemoselective functionalization of C(sp3)-H bonds enabled by organic dyes
    Wei, Guo
    Basheer, Chanbasha
    Tan, Choon-Hong
    Jiang, Zhiyong
    TETRAHEDRON LETTERS, 2016, 57 (34) : 3801 - 3809
  • [27] Copper-catalyzed radical relay in C(sp3)-H functionalization
    Zhang, Zuxiao
    Chen, Pinhong
    Liu, Guosheng
    CHEMICAL SOCIETY REVIEWS, 2022, 51 (05) : 1640 - 1658
  • [28] Metal-free oxidative functionalization of C(sp3)-H of ketones and alcohols for the synthesis of isoquinolinonediones
    Zhu, Su-Li
    Zhou, Ping-Xin
    Xia, Xiao-Feng
    RSC ADVANCES, 2016, 6 (68): : 63325 - 63330
  • [29] Recent advances in copper-mediated chelation-assisted functionalization of unactivated C-H bonds
    Rao, Wei-Hao
    Shi, Bing-Feng
    ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (08): : 1028 - 1047
  • [30] Copper-mediated C(sp3)-H amination in a multiple C-N bond-forming strategy for the synthesis of N-heterocycles
    Xie, Zeqiang
    Peng, Jiangling
    Zhu, Qiang
    ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (01): : 82 - 86