Visible-light-induced decarboxylative alkylation of quinoxalin-2(1H)-ones with phenyliodine(III) dicarboxylates by cerium photocatalysis

被引:15
|
作者
Zhang, Lixi [1 ,2 ]
He, Jingwen [1 ]
Zhang, Pengfei [3 ]
Zheng, Kai [2 ]
Shen, Chao [2 ]
机构
[1] Zhejiang Univ Technol, Coll Environm, Hangzhou 310032, Zhejiang, Peoples R China
[2] Zhejiang Shuren Univ, Coll Biol & Environm Engn, Hangzhou 310015, Peoples R China
[3] Hangzhou Normal Univ, Minist Educ, Coll Mat Chem & Chem Engn, Key Lab Organosilicon Chem & Mat Technol, Hangzhou 311121, Peoples R China
基金
中国国家自然科学基金;
关键词
Visible light; Decarboxylative alkylation; Cerium catalysis; Quinoxalin-2(1H)-ones; QUINOXALINE DERIVATIVES; INHIBITORS; METAL; ARYLATION; DESIGN;
D O I
10.1016/j.mcat.2022.112145
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Despite advances in the photoredox catalysis using organic dyes or expensive Ir and Ru complexes, the discovery and employment of photocatalysts based on alternative and abundant metal salts remain highly necessary. Herein, the visible-light-induced decarboxylative alkylation of quinoxalin-2(1H)-ones with phenyliodine(III) dicarboxylate has been accomplished using inexpensive and catalytic amount of CeCl3 as the photocatalyst. The novel protocol has advantages of mild conditions, high yields and good substrate scope. Control experiments indicate that a radical mechanism is responsible for the present transformation.
引用
收藏
页数:4
相关论文
共 50 条
  • [1] Visible-Light-Initiated Decarboxylative Alkylation of Quinoxalin-2(1H)-ones with Phenyliodine(III) Dicarboxylates in Recyclable Ruthenium(II) Catalytic System
    Xie, Long-Yong
    Jiang, Li-Lin
    Tan, Jia-Xi
    Wang, Yi
    Xu, Xiang-Qin
    Zhang, Bo
    Cao, Zhong
    He, Wei-Min
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2019, 7 (16) : 14153 - 14160
  • [2] Photocatalyst-free visible light induced decarboxylative alkylation of quinoxalin-2(1H)-ones with carboxylic acids
    Hong, Yun-Yun
    Peng, Zhen
    Ma, Hui
    Zhu, Qi
    Xu, Xiang-Qin
    Yang, Li-Hua
    Xie, Long-Yong
    TETRAHEDRON LETTERS, 2022, 89
  • [3] Visible-light induced decarboxylative alkylation of quinoxalin-2(1H)-ones at the C3-position
    Xue, Wenxuan
    Su, Yingpeng
    Wang, Ke-Hu
    Zhang, Rong
    Feng, Yawei
    Cao, Lindan
    Huang, Dangfeng
    Hu, Yulai
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (27) : 6654 - 6661
  • [4] Visible-light-induced C-H sulfenylation of quinoxalin-2(1H)-ones with disulfides by sustainable cerium catalysis
    Zhang, Lixi
    Zhang, Pengfei
    Zhu, Dancheng
    Zheng, Kai
    Shen, Chao
    GREEN SYNTHESIS AND CATALYSIS, 2023, 4 (03): : 226 - 230
  • [5] Catalyst-free visible-light-induced decarbonylative C-H alkylation of quinoxalin-2(1H)-ones
    Shi, Xiaodi
    Cao, Yunpeng
    Liu, Yuxiu
    Niu, Kaikai
    Song, Hongjian
    Zhang, Jingjing
    Wang, Qingmin
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (05) : 1296 - 1300
  • [6] Visible-Light-Induced Singlet Oxygen-Promoted Arylation and Alkylation of Quinoxalin-2(1H)-ones and Quinolines
    Tan, Renjun
    Yang, Hequn
    Jiang, Min
    Song, Peijun
    MOLECULES, 2024, 29 (21):
  • [7] Visible-Light-Induced Direct C-H Amination of Quinoxalin-2(1H)-ones
    Liu, Yanpeng
    Pei, Congcong
    Chen, Xiaoyu
    Zhang, Jianye
    Li, Jingya
    Zou, Dapeng
    Wu, Yangjie
    Wu, Yusheng
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (05) : 709 - 714
  • [8] Photoelectrochemical Decarboxylative C-H Alkylation of Quinoxalin-2(1H)-ones
    Niu, Kaikai
    Zhou, Pan
    Ding, Ling
    Hao, Yanke
    Liu, Yuxiu
    Song, Hongjian
    Wang, Qingmin
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2021, 9 (49) : 16820 - 16828
  • [9] Visible-light-induced tandem reaction of quinoxalin-2(1H)-ones, alkenes, and sulfonyl chlorides
    Lu, Yaru
    Li, Meng
    Feng, Qianqian
    Zhang, Ziqin
    Zhang, Zhenting
    Lu, Kui
    Liu, Zhengyu
    Zhao, Xia
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (33) : 6799 - 6809
  • [10] Visible-Light-Induced Alkoxylation of Quinoxalin-2(1H)-ones with Alcohols for the Synthesis of Heteroaryl Ethers
    Zhao, Lulu
    Wang, Lei
    Gao, Yanhui
    Wang, Zhiming
    Li, Pinhua
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (23) : 5363 - 5370