Visible-Light-Promoted Palladium-Catalyzed C-H Amination for the Synthesis of Carbazolequinones

被引：2
作者：
Han Yang [1 ]
Jiang Weichao [1 ]
Zhang Jing [1 ]
Peng Jinsong [1 ]
Chen Chunxia [1 ]
机构：
[1] Northeast Forestry Univ, Coll Chem Chem Engn & Resource Utilizat, Harbin 150040, Peoples R China
来源：
CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 42卷 / 01期
关键词：
light-promoted; palladium-catalyzed; C-H amination; carbazolequinones; CALOTHRIXINS; ARYLATION; ARENES; ARYL;
D O I：
10.6023/cjoc202104037
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An intramolecular palladium-catalyzed cross-dehydrogenative C-H amination under blue LED irradiation at room temperature was developed. With oxygen as the external oxidant, a broad range of functional groups was compatible with the aromatic C-H amination of 2-amino-3-arylnaphthalene-1,4-diones, and diverse carbazolequinones can be obtained with good yields and excellent regioselectivity.
引用
收藏
页码：266 / 276
页数：11
相关论文
共 51 条
  • [1] Concise Total Synthesis of Calothrixins A and B
    Abe, Takumi
    Ikeda, Toshiaki
    Yanada, Reiko
    Ishikura, Minoru
    [J]. ORGANIC LETTERS, 2011, 13 (13) : 3356 - 3359
  • [2] Transition metal mediated selective C vs N arylation of 2-aminonaphthoquinone and its application toward the synthesis of benzocarbazoledione
    Ashok, Polu
    Ilangovan, Andivelu
    [J]. TETRAHEDRON LETTERS, 2018, 59 (05) : 438 - 441
  • [3] A Unified Modular Synthetic Strategy for Dictyodendrins F, H, I, and G
    Banne, Sreenivas
    Reddy, D. Prabhakar
    Li, Wenxi
    Wang, Chenhui
    Guo, Jian
    He, Yun
    [J]. ORGANIC LETTERS, 2017, 19 (18) : 4996 - 4999
  • [4] Synthesis, electrochemistry, and bioactivity of the cyanobacterial calothrixins and related quinones
    Bernardo, PH
    Chai, CLL
    Heath, GA
    Mahon, PJ
    Smith, GD
    Waring, P
    Wilkes, BA
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (20) : 4958 - 4963
  • [5] Novel Synthesis of 5-Substituted 5H-Benzo[b] carbazole-6,11-diones via Double Buchwald-Hartwig Reaction
    Bolibrukh, Khrystyna
    Khoumeri, Omar
    Polovkovych, Svyatoslav
    Novikov, Volodymyr
    Terme, Thierry
    Vanelle, Patrice
    [J]. SYNLETT, 2014, 25 (19) : 2765 - 2768
  • [6] Catalytic direct arylation with aryl chlorides, bromides, and iodides: Intramolecular studies leading to new intermolecular reactions
    Campeau, LC
    Parisien, M
    Jean, A
    Fagnou, K
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (02) : 581 - 590
  • [7] Recent Advances in Photocatalytic C-N Bond Coupling Reactions
    Chan, Chun-Ming
    Chow, Yip-Chi
    Yu, Wing-Yiu
    [J]. SYNTHESIS-STUTTGART, 2020, 52 (20): : 2899 - 2921
  • [8] A One-Pot Approach to 2-(N-Substituted Amino)-1,4-naphthoquinones with Use of Nitro Compounds and 1,4-Naphthoquinones in Water
    Chen, Xu-Ling
    Dong, Yu
    He, Shuai
    Zhang, Rui
    Zhang, Hua
    Tang, Lei
    Zhang, Xiao-Mei
    Wang, Ji-Yu
    [J]. SYNLETT, 2019, 30 (05) : 615 - 619
  • [9] Visible-Light-Promoted Aerobic Homogenous Oxygenation Reactions
    Cheng, Xiaokai
    Hu, Xingen
    Lu, Zhan
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (02) : 251 - 266
  • [10] Synthesis of Carbazoles by a Merged Visible Light Photoredox and Palladium-Catalyzed Process
    Choi, Sungkyu
    Chatterjee, Tanmay
    Choi, Won Joon
    You, Youngmin
    Cho, Eun Jin
    [J]. ACS CATALYSIS, 2015, 5 (08): : 4796 - 4802
123456