π-Extension of Isoindigos (IIDs) through C-H/N-H Activation and Alkyne Annulation†

被引：0
|
作者：
Wang, Kang [1 ]
Chen, Liangliang [2 ]
Huang, Yan-Ying [2 ,3 ]
Qin, Liyuan [2 ,3 ]
Li, Cheng [2 ]
Zhang, Xi-Sha [2 ,3 ,4 ]
Luo, Feixian [5 ]
Duan, Zheng [1 ]
Zhang, Guanxin [2 ]
Zhang, Deqing [2 ,3 ]
机构：
[1] Zhengzhou Univ, Coll Chem, Green Catalysis Ctr, Zhengzhou 450000, Henan, Peoples R China
[2] Chinese Acad Sci, Beijing Natl Lab Mol Sci, Inst Chem, CAS Key Lab Organ Solids, Beijing 100190, Peoples R China
[3] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
[4] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
[5] Minzu Univ China, Key Lab Ecol & Environm Minor Areas, Natl Ethn Affairs Commiss, Beijing 100081, Peoples R China
来源：
NEW YORK JOURNAL OF MATHEMATICS | 2023年 / 29卷
关键词：
Isoindigo; C-H; N-H activation; Alkyne annulation; Opto-electronic function; Synthetic methods; Functionalized Units;
D O I：
暂无
中图分类号：
O1 [数学];
学科分类号：
0701 ; 070101 ;
摘要：
Comprehensive Summary Isoindigo (IID) is widely used as organic dye and conjugated unit in opto-electronic materials. Functionalization of IID to increase its structural complexity is demanding for obtaining diversity properties. Herein, we developed a direct C-H/N-H activation method of IIDs via double alkyne annulations and synthesized pi -extended IIDs with two pairs of 5/7 membered rings. The structure of the pi -extended IIDs was characterized and confirmed by H-1 NMR, C-13 NMR, HRMS and X ray crystal analysis. Their physical properties were characterized by UV-vis absorption, cyclic voltammetry and thermogravimetric analysis. The absorption coefficient of the annulated products enhanced significantly compared with the non-annulated analogue.
引用
收藏
页码：2589 / 2596
页数：8
相关论文
共 50 条
  • [1] p-Extension of Isoindigos (IIDs) through C-H/N-H Activation and Alkyne Annulation&DAG;
    Wang, Kang
    Chen, Liangliang
    Huang, Yan-Ying
    Qin, Liyuan
    Li, Cheng
    Zhang, Xi-Sha
    Luo, Feixian
    Duan, Zheng
    Zhang, Guanxin
    Zhang, Deqing
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2023, 41 (20) : 2589 - 2596
  • [2] Iron-catalyzed C-H/N-H activation by triazole guidance: versatile alkyne annulation
    Cera, G.
    Haven, T.
    Ackermann, L.
    [J]. CHEMICAL COMMUNICATIONS, 2017, 53 (48) : 6460 - 6463
  • [3] Concise Synthesis of Lamellarin Alkaloids by C-H/N-H Activation: Evaluation of Metal Catalysts in Oxidative Alkyne Annulation
    Mei, Ruhuai
    Zhang, Shou-Kun
    Ackermann, Lutz
    [J]. SYNLETT, 2017, 28 (14) : 1715 - 1718
  • [4] π-Extended Polyaromatic Hydrocarbons by Sustainable Alkyne Annulations through Double C-H/N-H Activation
    Gonka, Elzbieta
    Yang, Long
    Steinbock, Ralf
    Pesciaioli, Fabio
    Kuniyil, Rositha
    Ackermann, Lutz
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (71) : 16246 - 16250
  • [5] Nickel-catalyzed alkyne annulation by anilines: versatile indole synthesis by C-H/N-H functionalization
    Song, Weifeng
    Ackermann, Lutz
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (59) : 6638 - 6640
  • [6] Challenges in oxidative C-H and N-H activation
    Kozlowski, Marisa C.
    Curto, John
    Padilla-Salinas, Rosaura
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [7] Cobalt-Catalyzed Oxidase C-H/N-H Alkyne Annulation: Mechanistic Insights and Access to Anticancer Agents
    Mei, Ruhuai
    Wang, Hui
    Warratz, Svenja
    Macgregor, Stuart A.
    Ackermann, Lutz
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (20) : 6759 - 6763
  • [8] Ruthenium(II)-Catalyzed C-H/N-H Alkyne Annulation of Nonsymmetric Imidazoles: Mechanistic Insights by Computation and Photophysical Properties
    Machado, Luana A.
    Paz, Esther R. S.
    Araujo, Maria H.
    Almeida, Leandro D.
    Bozzi, Icaro A. O.
    Dias, Gleiston G.
    Pereira, Cynthia L. M.
    Pedrosa, Leandro F.
    Fantuzzi, Felipe
    Martins, Felipe T.
    Cury, Luiz A.
    da Silva Junior, Eufranio N.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (28)
  • [9] Nickel-Catalyzed [4+2] Annulation of Nitriles and Benzylamines by C-H/N-H Activation
    Sikari, Rina
    Chakraborty, Gargi
    Guin, Amit Kumar
    Paul, Nanda D.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (01): : 279 - 290
  • [10] Synthesis of Polycyclic Isoindolines via α-C-H/N-H Annulation of Alicyclic Amines
    Paul, Anirudra
    Vasseur, Camille
    Daniel, Scott D.
    Seidel, Daniel
    [J]. ORGANIC LETTERS, 2022, 24 (05) : 1224 - 1227
12345