Iodine-Catalyzed Synthesis of N,N′-Chelate Organoboron Aminoquinolate

被引:8
|
作者
Yang, Tianbao [1 ]
Cao, Xin [1 ]
Zhang, Xing-Xing [1 ]
Ou, Yifeng [1 ]
Au, Chak-Tong [2 ]
Yin, Shuang-Feng [1 ]
Qiu, Renhua [1 ]
机构
[1] Hunan Univ, Coll Chem & Chem Engn, State Key Lab Chemo Biosensing & Chemometr, Adv Catalyt Engn Res Ctr,Minist Educ, Changsha 410082, Peoples R China
[2] Hunan Inst Engn, Coll Chem & Chem Engn, Xiangtan 411104, Hunan, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 19期
关键词
FLUORESCENT-PROBE; BODIPY; LUMINESCENCE; BROMINATION; TEMPERATURE; QUINOLINES; COMPLEXES; ARYLATION; POLYMERS; WATER;
D O I
10.1021/acs.joc.0c01649
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We disclose a novel method for the synthesis of fluorescent N, N'-chelate organoboron compounds in high efficiency by treatment of aminoquinolates with NaBAr4/R'COOH in the presence of an iodine catalyst. These compounds display high air and thermal stability. A possible catalytic mechanism based on the results of control experiments has been proposed. Fluorescence quantum yield of 3b is up to 0.79 in dichloromethane.
引用
收藏
页码:12430 / 12443
页数:14
相关论文
共 50 条
  • [21] Iodine-Catalyzed C-N Bond Formation: Synthesis of 3-Aminoquinoxalinones under Ambient Conditions
    Gupta, Abhishek
    Deshmukh, Mahesh Subhashrao
    Jain, Nidhi
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (09): : 4784 - 4792
  • [22] Iodine-catalyzed synthesis of pyrrole-substituted indolinone
    Banik, Bimal K.
    Morales, Frances
    Cardona, Magda
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [23] Iodine-Catalyzed Aza-Diels-Alder Reactions of Aliphatic N-Arylaldimines
    Rai, Niethnadka Premsai
    Shashikanth, S.
    Arunachalam, P. N.
    SYNTHETIC COMMUNICATIONS, 2009, 39 (12) : 2125 - 2136
  • [24] Mechanistic study on iodine-catalyzed aromatic bromination of aryl ethers by N-Bromosuccinimide
    Pramanick, Pranab Kumar
    Hou, Zhen-Lin
    Yao, Bo
    TETRAHEDRON, 2017, 73 (50) : 7105 - 7114
  • [25] Iodine-catalyzed synthesis of N,N-diaryl-o-phenylenediamines from cyclohexanones and anilines using DMSO and O2 as oxidants
    Xiong, Mingteng
    Gao, Zhan
    Liang, Xiao
    Cai, Pengfei
    Zhu, Heping
    Pan, Yuanjiang
    CHEMICAL COMMUNICATIONS, 2018, 54 (69) : 9679 - 9682
  • [26] Iodine-Catalyzed, Efficient Synthesis of -Hydroxy Phosphonates in Water
    Wang, Hong-She
    Zeng, Jun-E
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2010, 185 (07) : 1425 - 1428
  • [27] Iodine-catalyzed N-sulfonylation of benzotriazoles with sodium sulfinates under mild conditions
    Si-Xue Wu
    Yi-Kun Zhang
    Hong-Wei Shi
    Jie Yan
    Chinese Chemical Letters, 2016, 27 (09) : 1519 - 1522
  • [28] Iodine-Catalyzed Synthesis of Spiroorthcarbonates under Neutral Conditions
    Rahimizadeh, Mohammad
    Bakavoli, Mehdi
    Shiri, Ali
    Eshghi, Hossein
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2009, 30 (08) : 1699 - 1700
  • [29] Iodine-catalyzed N-sulfonylation of benzotriazoles with sodium sulfinates under mild conditions
    Wu, Si-Xue
    Zhang, Yi-Kun
    Shi, Hong-Wei
    Yan, Jie
    CHINESE CHEMICAL LETTERS, 2016, 27 (09) : 1519 - 1522
  • [30] Iodine-Catalyzed Mild and Efficient Method for the Synthesis of Chalcones
    Sashidhara, Koneni V.
    Rosaiah, Jammikuntla N.
    Kumar, Abdhesh
    SYNTHETIC COMMUNICATIONS, 2009, 39 (13) : 2288 - 2296