Copper-catalyzed chemoselective C-H functionalization of quinoxalin-2(1H)-ones with hexafluoroisopropanol

被引:22
|
作者
Su, Hai-Yan [1 ]
Zhu, Xiao-Lei [1 ]
Huang, Yangen [1 ]
Xu, Xiu-Hua [2 ]
Qing, Feng-Ling [1 ,2 ]
机构
[1] Donghua Univ, Coll Chem Chem Engn & Biotechnol, 2999 North Renmin Lu, Shanghai 201620, Peoples R China
[2] Chinese Acad Sci, Key Lab Organofluorine Chem, Ctr Excellence Mol Synth, Shanghai Inst Organ Chem,Univ Chinese Acad Sci, 345 Lingling Lu, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
FLUORINATED ALCOHOLS; QUINOXALINONES; PHOTOCATALYST; ALKOXYLATION; DERIVATIVES; INHIBITORS; ARYLATION; THIOLS;
D O I
10.1039/d0cc05623e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An unexpected three-component reaction of quinoxalin-2(1H)-ones,tert-butyl peroxybenzoate (TBPB), and hexafluoroisopropanol (HFIP) is described. Under CuBr-catalyzed and TBPB-oxidized conditions, a variety of hydroxyhexafluoroisobutylated quinoxalin-2(1H)-ones were formed. Furthermore, the first hexafluoroisopropoxylation of the quinoxalin-2(1H)-ones with HFIP is also demonstrated with Cu2O as the catalyst and PhI(OAc)(2)as the oxidant. These new transformations of HFIP furnish previously unknown and potentially useful fluorinated quinoxalin-2(1H)-one derivatives.
引用
收藏
页码:12805 / 12808
页数:4
相关论文
共 50 条
  • [1] Copper-catalyzed oxidative coupling of quinoxalin-2(1H)-ones with alcohols: access to hydroxyalkylation of quinoxalin-2(1H)-ones
    Fu, Junhao
    Yuan, Jinwei
    Zhang, Yue
    Xiao, Yongmei
    Mao, Pu
    Diao, Xiaoqiong
    Qu, Lingbo
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (23): : 3382 - 3390
  • [2] Copper-catalyzed C-3 benzylation of quinoxalin-2(1H)-ones with benzylsulfonyl hydrazides
    Xie, Dong
    Tian, Ren-Gui
    Zhang, Xue-Ting
    Tian, Shi-Kai
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (22) : 4518 - 4521
  • [3] Metal-Free Direct C-H Functionalization of Quinoxalin-2(1H)-Ones to Produce 3-Vinylated Quinoxalin-2(1H)-Ones in the Presence of Alkenes
    Ding, Rongcai
    Li, Yingxue
    Chang, Yaoyao
    Liu, Yue
    Yu, Jie
    Lv, Yanna
    Hu, Jinxing
    FRONTIERS IN CHEMISTRY, 2021, 9
  • [4] 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
  • [5] Copper-Catalyzed Alkylation of Quinoxalin-2(1H )-ones with Styrenes and tert -Butyl Peroxybenzoate
    Zhong, Xiaoyang
    Li, Xinying
    Yao, Hua
    Yan, Zhaohua
    Guo, Hui
    Min, Li
    Lin, Sen
    SYNLETT, 2022, 33 (10) : 998 - 1002
  • [6] Transition-metal free direct C-H functionalization of quinoxalin-2(1H)-ones with oxamic acids leading to 3-carbamoyl quinoxalin-2(1H)-ones
    Yuan, Jin-Wei
    Zhu, Jun-Liang
    Zhu, Hu-Lin
    Peng, Fang
    Yang, Liang-Yu
    Mao, Pu
    Zhang, Shou-Ren
    Li, Yan-Chun
    Qu, Ling-Bo
    ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (02): : 273 - 285
  • [7] 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
  • [8] 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
  • [9] Recent Advances on the Catalytic Functionalization of Quinoxalin-2(1H)-ones via C-H Bond Activation
    Mao, Pu
    Zhu, Junliang
    Yuan, Jinwei
    Yang, Liangru
    Xiao, Yongmei
    Zhang, Changsen
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (06) : 1529 - 1547
  • [10] Copper-catalyzed C-H/N-H cross-coupling reactions for the synthesis of 3-heteroaryl quinoxalin-2(1H)-ones
    Guo, Tao
    Wang, Chuan-Chuan
    Fu, Xiang-Heng
    Liu, Yu
    Zhang, Pan-Ke
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (13) : 3333 - 3337