Porous Organic Polymer Supported Nano Ruthenium Catalysts for Cascade Aromatization of Quinoxalin-2(1H)-one and C-H Annulation with Alkynes

被引:4
|
作者
Huang, Ziwei [1 ]
Xian, Jiayi [1 ]
Lv, Shaohuan [1 ]
Xu, Shanshan [1 ]
Li, Jiefang [1 ]
Xie, Feng [1 ]
Li, Bin [1 ,2 ]
机构
[1] Wuyi Univ, Sch Biotechnol & Hlth Sci, Jiangmen 529020, Guangdong, Peoples R China
[2] Wuyi Univ, Sch Biotechnol & Hlth Sci, Guangdong Prov Key Lab Large Anim Models Biomed, Jiangmen 529020, Peoples R China
关键词
OXIDATIVE ANNULATION; BOND ACTIVATION; RU; ACCESS;
D O I
10.1021/acs.orglett.3c03056
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Selective C-H annulation with alkynes is one of the most useful tools to synthesize heterocycles. Herein, we developed novel porous organic polymers supported ruthenium (POPs-Ru) as highly efficient catalysts for cascade aromatization of quinoxalin-2-(1H)-one and C-H annulation with alkynes. Both terminal and internal alkynes were successfully transferred to furo-[2,3-b]-quinoxaline derivatives with good functional group tolerance and high regioselectivity by using POPs-Ru catalysts. Furthermore, the catalyst exhibited high activity and could be reused at least five times without obvious deactivation of this coupling reaction. This study offers an important platform for the immobilization of molecular metal catalysts for C-H functionalization.
引用
收藏
页码:7974 / 7978
页数:5
相关论文
共 50 条
  • [21] C-H benzylation of quinoxalin-2(1H)-ones via visible-light riboflavin photocatalysis
    Yan, Qiuli
    Cui, Wenwen
    Li, Junxin
    Xu, Guiyun
    Song, Xiuyan
    Lv, Jian
    Yang, Daoshan
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (10): : 2653 - 2658
  • [22] Electrochemical C-H functionalization to synthesize 3-hydroxyalkylquinoxalin-2(1H)-ones via quinoxalin-2(1H)-ones and aldehydes
    Liu, Han-Fu
    He, Mu-Xue
    Tang, Hai-Tao
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (21): : 5955 - 5961
  • [23] Direct C-H Cyanoalkylation of Quinoxalin-2(1H)-ones via Radical C-C Bond Cleavage
    Yang, Lin
    Gao, Pin
    Duan, Xin-Hua
    Gu, Yu-Rui
    Guo, Li-Na
    ORGANIC LETTERS, 2018, 20 (04) : 1034 - 1037
  • [24] Solvatochromic effect on photophysical properties of Quinoxalin-2(1H)-one and 3-Benzylquinoxalin-2(1H)-one
    R. Jdaa
    B. Benali
    A. El Assyry
    B. Lakhrissi
    Optical and Quantum Electronics, 2017, 49
  • [25] Solvatochromic effect on photophysical properties of Quinoxalin-2(1H)-one and 3-Benzylquinoxalin-2(1H)-one
    Jdaa, R.
    Benali, B.
    El Assyry, A.
    Lakhrissi, B.
    OPTICAL AND QUANTUM ELECTRONICS, 2017, 49 (02)
  • [26] Ruthenium catalyzed oxidative annulation with alkynes via cascade C-H/N-H bond functionalizations
    Wang, Rui
    Falck, J. R.
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2014, 759 : 33 - 36
  • [27] Visible-light-promoted direct C-H/S-H cross-coupling of quinoxalin-2(1H)-ones with thiols leading to 3-sulfenylated quinoxalin-2(1H)-ones in air
    Xie, Long-Yong
    Chen, Yan-Ling
    Qin, Li
    Wen, Yuan
    Xie, Jian-Wei
    Tan, Jia-Xi
    Huang, Ying
    Cao, Zhong
    He, Wei-Min
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (24) : 3950 - 3955
  • [28] Direct C-H Trifluoromethylation of Quinoxalin-2(1H)-ones under Transition-Metal-Free Conditions
    Wang, Liping
    Zhang, Yuecheng
    Li, Fanfan
    Hao, Xinyu
    Zhang, Hong-Yu
    Zhao, Jiquan
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (20) : 3969 - 3977
  • [29] Recent Developments in Direct C-H Functionalization of Quinoxalin-2(1H)-Ones via Heterogeneous Catalysis Reactions
    Yang, Qiming
    Wang, Hu
    Wang, Xiang
    Lei, Yizhu
    MOLECULES, 2023, 28 (13):
  • [30] Visible light-induced direct and highly selective C-H functionalization of quinoxalin-2(1H)-one without orientating group
    Hou, Huiqing
    Wang, Changsheng
    Cheng, Xin
    Chen, Houzheng
    Sun, Weiming
    Zheng, Zhiqiang
    Ke, Fang
    CATALYSIS SCIENCE & TECHNOLOGY, 2023, 13 (02) : 305 - 309