B(C6F5)3-Catalyzed [4+2] Cyclization Strategy: Synthesis and Photophysical Properties of 5H-Naphtho[2,3-c]carbazole-8,13-dione Derivatives

被引：10
|
作者：
Xu, Hong [1 ,2 ,3 ]
Wang, Bei [1 ,2 ,3 ]
Li, Fu-Yu [1 ,2 ,3 ]
Wang, Ji-Yu [1 ,2 ]
机构：
[1] Xihua Univ, Dept Chem, Chengdu 610039, Peoples R China
[2] Chengdu Inst Organ Chem, Chinese Acad Sci, Asymmetr Synth & Chiraltechnol Key Lab Sichuan Pro, Chengdu 610041, Peoples R China
[3] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 05期
关键词：
DIELS-ALDER REACTION; DIASTEREOSELECTIVE SYNTHESIS; CARBAZOLE ALKALOIDS; ORGANIC-SYNTHESIS; C-C; INDOLE; CONSTRUCTION; INHIBITORS; ANNULATION; REACTIVITY;
D O I：
10.1021/acs.joc.2c02064
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In this paper, a series of novel carbazolequinones were efficiently obtained by a B(C6F5)3-catalyzed [4 + 2] cyclization reaction. This protocol not only had a simple operation, broad substrate range, and high atomic economy, but also had a low catalyst loading and avoided using metal catalysts. In addition, we constructed diverse new carbazole-fused compounds under different reduction conditions. The results of photophysical characterization showed that the structure of carbazole-fused derivatives had a significant impact on the fluorescence properties.
引用
收藏
页码：2703 / 2713
页数：11
相关论文
共 50 条
  • [31] B(C6F5)3-catalyzed β-C(sp3)-H alkylation of tertiary amines with 2-aryl-3H-indol-3-ones
    Zou, Chang-Peng
    Ma, Tao
    Qiao, Xiu-Xiu
    Wu, Xi-Xi
    Li, Ganpeng
    He, Yonghui
    Zhao, Xiao-Jing
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (21) : 4393 - 4397
  • [32] Synthesis, structure, and application of [PhNMe2H][B{C6F4C(C6F5)2F}4]
    Rodriguez, G
    Brant, P
    ORGANOMETALLICS, 2001, 20 (11) : 2417 - 2420
  • [33] From B(C6F5)3 to B(OC6F5)3:: Synthesis of (C6F5)2BOC6F5 and C6F5B(OC6F5)2 and their relative lewis acidity
    Britovsek, GJP
    Ugolotti, J
    White, AJP
    ORGANOMETALLICS, 2005, 24 (07) : 1685 - 1691
  • [34] Reaction of B(C6F5)3 with zirconium and hafnium benzyl diene complexes.: The crystal and molecular structures of Cp"Zr(C6F5) {η4-CH2CMeCHCHB(C6F5)2} and [Cp"Hf(2,3Me2C4H4)(OEt2)][PhCH2B(C6F5)3] [Cp"=1,3-(SiMe3)2C5H3]
    Pindado, GJ
    Thornton-Pett, M
    Hursthouse, MB
    Coles, SJ
    Bochmann, M
    JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1999, (10): : 1663 - 1668
  • [35] B(C6F5)3-catalyzed O-H insertion reactions of diazoalkanes with phosphinic acids
    Zhang, Yangyang
    Zhang, Xinzhi
    Zhao, Jincheng
    Jiang, Jun
    Organic and Biomolecular Chemistry, 2021, 19 (26): : 5772 - 5776
  • [36] B(C6F5)3-catalyzed O-H insertion reactions of diazoalkanes with phosphinic acids
    Zhang, Yangyang
    Zhang, Xinzhi
    Zhao, Jincheng
    Jiang, Jun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (26) : 5772 - 5776
  • [37] B(C6F5)3-Catalyzed C-Si/Si-H Cross-Metathesis of Hydrosilanes
    Ma, Yuanhong
    Zhang, Liang
    Luo, Yong
    Nishiura, Masayoshi
    Hou, Zhaomin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (36) : 12434 - 12437
  • [38] STEREOSPECIFIC POLYMERIZATION OF METHYL-METHACRYLATE INITIATED BY DIMETHYLZIRCONOCENE/B(C6F5)(3) (OR PH(3)CB(C6F5)(4))/ZN(C2H5)(2)
    SOGA, K
    DENG, H
    YANO, T
    SHIONO, T
    MACROMOLECULES, 1994, 27 (26) : 7938 - 7940
  • [39] B(C6F5)3-Catalyzed Conjugate Addition Reactions: Addition of C-H Aromatics as Nucleophiles to Nitroalkenes
    Qi, Liang
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 56 (01) : 169 - 173
  • [40] A new type of light-emitting naphtho[2,3-c][1,2,5] thiadiazole derivatives:: synthesis, photophysical characterization and transporting properties
    Wei, Peng
    Duan, Lian
    Zhang, Deqiang
    Qiao, Juan
    Wang, Liduo
    Wang, Ruji
    Dong, Guifang
    Qiu, Yong
    JOURNAL OF MATERIALS CHEMISTRY, 2008, 18 (07) : 806 - 818
12345