Visible-light-induced three-component reaction of quinoxalin-2(1H)-ones, alkenes and CF3SO2Na leading to 3-trifluoroalkylated quinoxalin-2(1H)-ones

被引：157
作者：
Meng, Na [1 ]
Lv, Yufen [1 ]
Liu, Qishun [1 ]
Liu, Ruisheng [1 ]
Zhao, Xiaohui [2 ,3 ]
Wei, Wei [1 ,2 ,3 ]
机构：
[1] Qufu Normal Univ, Sch Chem & Chem Engn, Qufu 273165, Shandong, Peoples R China
[2] Chinese Acad Sci, Northwest Inst Plateau Biol, Qinghai Prov Key Lab Tibetan Med Res, Xining 810008, Qinghai, Peoples R China
[3] Chinese Acad Sci, Northwest Inst Plateau Biol, Key Lab Tibetan Med Res, Xining 810008, Qinghai, Peoples R China
来源：
CHINESE CHEMICAL LETTERS | 2021年 / 32卷 / 01期
关键词：
Metal-free; Visible-light-catalysis; Three-component reaction; Quinoxalin-2(1H)-ones; INDUCED DEOXYGENATIVE C2-SULFONYLATION; C-H TRIFLUOROMETHYLATION; QUINOLINE N-OXIDES; METAL; DESIGN; QUINOXALIN-2(H)-ONES; ARYLATION; ANTITUMOR; FLUORINE; OXIDANT;
D O I：
10.1016/j.cclet.2020.11.034
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A facile and metal-free visible-light-enabled three-component reaction of quinoxalin-2(1H)-ones, alkenes and CF3SO2Na has been developed under air at room temperature. This photocatalytic tandem reaction using 4CzIPN as the photocatalyst and air as the green oxidant, provides a mild and environmentally friendly approach to access a series of 3-trifluoroalkylated quinoxalin-2(1H)-ones. (C) 2020 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
引用
收藏
页码：258 / 262
页数：5
相关论文
共 77 条
[51]   Visible Light-Induced Photocatalytic C-H Perfluoroalkylation of Quinoxalinones under Aerobic Oxidation Condition [J].
Wei, Zhenjiang ;
Qi, Sijia ;
Xu, Yanhao ;
Liu, Hao ;
Wu, Junzhen ;
Li, Hongshuang ;
Xia, Chengcai ;
Duan, Guiyun .
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (23) :5490-5498
[52]   C(sp2)-H/O-H cross-dehydrogenative coupling of quinoxalin-2(1H)-ones with alcohols under visible-light photoredox catalysis [J].
Xie, Long-Yong ;
Liu, Yi-Shu ;
Ding, Hong-Ru ;
Gong, Shao-Feng ;
Tan, Jia-Xi ;
He, Jun-Yi ;
Cao, Zhong ;
He, Wei-Min .
CHINESE JOURNAL OF CATALYSIS, 2020, 41 (08) :1168-1173
[53]   Visible-light-induced decarboxylative acylation of quinoxalin-2(1H)-ones with α-oxo carboxylic acids under metal-, strong oxidant- and external photocatalyst-free conditions [J].
Xie, Long-Yong ;
Bai, You-Shu ;
Xu, Xiang-Qin ;
Peng, Xia ;
Tang, Hai-Shan ;
Huang, Ying ;
Lin, Ying-Wu ;
Cao, Zhong ;
He, Wei-Min .
GREEN CHEMISTRY, 2020, 22 (05) :1720-1725
[54]   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 [J].
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
[55]   Visible-Light-Initiated Decarboxylative Alkylation of Quinoxalin-2(1H)-ones with Phenyliodine(III) Dicarboxylates in Recyclable Ruthenium(II) Catalytic System [J].
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
[56]   Visible-light-induced deoxygenative C2-sulfonylation of quinoline N-oxides with sulfinic acids [J].
Xie, Long-Yong ;
Fang, Tai-Gang ;
Tan, Jia-Xi ;
Zhang, Bo ;
Cao, Zhong ;
Yang, Li-Hua ;
He, Wei-Min .
GREEN CHEMISTRY, 2019, 21 (14) :3858-3863
[57]   Metal-free C3-alkoxycarbonylation of quinoxalin-2(1H)-ones with carbazates as ecofriendly ester sources [J].
Xie, Long-Yong ;
Peng, Sha ;
Fan, Tai-Gang ;
Liu, Yan-Fang ;
Sun, Meng ;
Jiang, Li-Lin ;
Wang, Xing-Xing ;
Cao, Zhong ;
He, Wei-Min .
SCIENCE CHINA-CHEMISTRY, 2019, 62 (04) :460-464
[58]   Transition-Metal and Solvent-Free Oxidative C-H Fluoroalkoxylation of Quinoxalinones with Fluoroalkyl Alcohols [J].
Xu, Jun ;
Yang, Huiyong ;
Cai, Heng ;
Bao, Hanyang ;
Li, Wanmei ;
Zhang, Pengfei .
ORGANIC LETTERS, 2019, 21 (12) :4698-4702
[59]   Phenyliodonium Diacetate Mediated Carbotrifluoromethylation of Quinoxalin-2(1H)-ones [J].
Xue, Wenxuan ;
Su, Yingpeng ;
Wang, Ke-Hu ;
Cao, Lindan ;
Feng, Yawei ;
Zhang, Weigang ;
Huang, Danfeng ;
Hu, Yulai .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 8 (06) :887-892
[60]   Direct C-H Cyanoalkylation of Quinoxalin-2(1H)-ones via Radical C-C Bond Cleavage [J].
Yang, Lin ;
Gao, Pin ;
Duan, Xin-Hua ;
Gu, Yu-Rui ;
Guo, Li-Na .
ORGANIC LETTERS, 2018, 20 (04) :1034-1037
12345678