Manganese(I)-Catalyzed Direct Addition of C(sp3)-H Bonds to Aryl Isocyanates

被引:0
|
作者
Liu, Hongxin [1 ]
Yu, Zhichao [1 ]
Li, Bin [1 ]
Wang, Baiquan [1 ,2 ]
机构
[1] Nankai Univ, Coll Chem, State Key Lab Elemento Organ Chem, Tianjin 300071, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 18期
基金
中国国家自然科学基金;
关键词
C-H BOND; DIRECT NUCLEOPHILIC-ADDITION; CYCLIZATION DIRECT SYNTHESIS; CATALYZED DIRECT ADDITION; HETEROAROMATIC-COMPOUNDS; VERSATILE ROUTE; ORTHO-AMIDATION; MANGANESE; ACTIVATION; AMINOCARBONYLATION;
D O I
10.1021/acs.joc.4c01581
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The addition of C-H bonds to isocyanates catalyzed by transition metals is a highly auspicious methodology for providing synthetically and biologically important amides. However, the substrates are limited to C(sp(2))-H bonds. In this work, an efficient manganese(I)-catalyzed direct addition reaction of C(sp(3))-H bonds of 8-methylquinolines to aryl isocyanates has been developed, leading to the synthesis of various alpha-quinolinyl amide compounds in moderate to high yields. The reaction has a broad range of substrates and a good functional group tolerance. A possible mechanism is proposed based on the experimental results.
引用
收藏
页码:13429 / 13437
页数:9
相关论文
共 50 条
  • [41] Iron-Catalyzed Regioselective Borylation of C(sp3)-H Bonds
    Wang Dongping
    Jia Zhenhua
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (05) : 1697 - 1698
  • [42] Organopotassium-Catalyzed Silylation of Benzylic C(sp3)-H Bonds
    Neil, Baptiste
    Saadi, Lamine
    Fensterbank, Louis
    Chauvier, Clement
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (31)
  • [43] Iron-Catalyzed Carbenoid Insertion into C(sp3)-H Bonds
    Cheng, Qing-Qing
    Yang, Ji-Min
    Xu, Huan
    Zhu, Shou-Fei
    SYNLETT, 2017, 28 (11) : 1327 - 1330
  • [44] Photochemically Induced Radical Transformation of C(sp3)-H Bonds to C(sp3)-CN Bonds
    Kamijo, Shin
    Hoshikawa, Tamaki
    Inoue, Masayuki
    ORGANIC LETTERS, 2011, 13 (21) : 5928 - 5931
  • [45] Palladium-Catalyzed Direct Ethynylation of C(sp3)-H Bonds in Aliphatic Carboxylic Acid Derivatives
    Ano, Yusuke
    Tobisu, Mamoru
    Chatani, Naoto
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (33) : 12984 - 12986
  • [46] Copper-catalyzed direct monofluoroalkenylation of C(sp3)-H bonds via decarboxylation of α-fluoroacrylic acids
    Lu, Xiao-Yu
    Chen, Xing-Ke
    Gao, Meng-Ting
    Sun, Xiao-Mei
    Jiang, Run-Chuang
    Wang, Jun-Chao
    Yu, Li-Juan
    Ge, Meng-Yuan
    Wei, Zheng-Huan
    Liu, Zi
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (17) : 4712 - 4718
  • [47] Catalytic alkylation of unactivated C(sp3)-H bonds for C(sp3)-C(sp3) bond formation
    Chen, Zhen
    Rong, Meng-Yu
    Nie, Jing
    Zhu, Xue-Feng
    Shi, Bing-Feng
    Ma, Jun-An
    CHEMICAL SOCIETY REVIEWS, 2019, 48 (18) : 4921 - 4942
  • [48] Palladium-Catalyzed Direct Acyloxylation of C(sp2)-H and C(sp3)-H Bonds under the Assistance of Oxalyl Amide
    Zheng, Yongxiang
    Han, Jian
    Huang, Zhibin
    Shi, Daqing
    Zhao, Yingsheng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (08) : 2066 - 2072
  • [49] Photoinduced direct 4-pyridination of C(sp3)-H Bonds
    Hoshikawa, Tamaki
    Inoue, Masayuki
    CHEMICAL SCIENCE, 2013, 4 (08) : 3118 - 3123
  • [50] Cleavage of sp3 C-O Bonds via Oxidative Addition of C-H Bonds
    Choi, Jongwook
    Choliy, Yuriy
    Zhang, Xiawei
    Emge, Thomas J.
    Krogh-Jespersen, Karsten
    Goldman, Alan S.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (43) : 15627 - +