Copper-catalyzed redox neutral ketoalkylation of Csp2-H bonds via C-C bond cleavage

被引:11
作者
Chen, He
Guo, Li-Na
Sun, Qing-Xin
Chen, Lei
Tao, Jing-Qi
Gao, Pin [1 ]
机构
[1] Xi An Jiao Tong Univ, Xian Key Lab Sustainable Energy Mat Chem, Sch Chem, Dept Chem, Xian 710049, Peoples R China
基金
中国国家自然科学基金; 中国博士后科学基金;
关键词
HETEROAROMATIC N-OXIDES; CYCLOALKYLSILYL PEROXIDES; H FUNCTIONALIZATION; ALKYLATION; INHIBITORS; QUINOXALIN-2(1H)-ONES; DERIVATIVES; CYCLIZATION; QUINONES; RADICALS;
D O I
10.1039/d1qo00882j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient copper-catalyzed ketoalkylation of Csp(2)-H bonds with cycloalkyl silyl peroxides under mild and redox neutral conditions is presented. Relying on the C-C bond cleavage, a series of distal ketoalkyl moieties were successfully incorporated into the specific position of quinoxalin-2(1H)-ones, heteroaromatic N-oxides and quinones with moderate to good yields.
引用
收藏
页码:5866 / 5871
页数:6
相关论文
共 50 条
  • [31] Copper-Catalyzed Domino C-C Bond Cleavage of 2,3-Unsubstituted Indoles/Indolines and Oxindoles via Oxidation and Directed Insertion of 2-Aminopyridines: Direct Access to Quinazolinediones
    Ravi, Owk
    Ramaraju, Andhavaram
    Sridhar, Balasubramanian
    Bathula, Surendar Reddy
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (16) : 3009 - 3014
  • [32] Rh(II)-catalyzed intermolecular carboamination of pyridines via double Csp2-H bond activations
    Luo, Zhongfeng
    Jiang, Jingxing
    Zou, Lifang
    Zhou, Xiaoyu
    Liu, Junshan
    Ke, Zhuofeng
    Chen, Fengjuan
    Jiang, Huanfeng
    Zeng, Wei
    SCIENCE CHINA-CHEMISTRY, 2024, 67 (01) : 374 - 382
  • [33] γ-Functionalizations of Amines through Visible-Light-Mediated, Redox-Neutral C-C Bond Cleavage
    Shu, Wei
    Genoux, Alexandre
    Li, Zhaodong
    Nevado, Cristina
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (35) : 10521 - 10524
  • [34] Iron-Catalyzed Thiolation and Selenylation of Cycloalkyl Hydroperoxides via C-C Bond Cleavage
    Sun, Qing-Xin
    Chen, He
    Liu, Shuai
    Wang, Xiao-Qiang
    Duan, Xin-Hua
    Guo, Li-Na
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (17) : 11987 - 11997
  • [35] Iron-Catalyzed C-C Bond Cleavage and C-N Bond Formation
    Li, Wenjuan
    Zheng, Xiaojian
    Li, Zhiping
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (01) : 181 - 190
  • [36] Csp3-H monofluoroalkenylation via stereoselective C-F bond cleavage
    Hu, Ying
    Liu, Xingchen
    Ren, Zhouyang
    Hu, Binjing
    Li, Jie
    CHEMICAL COMMUNICATIONS, 2022, 58 (16) : 2734 - 2737
  • [37] Iron-Catalyzed π-Activated C-O Ether Bond Cleavage with C-C and C-H Bond Formation
    Fan, Xiaohui
    Cui, Xiao-Meng
    Guan, Yong-Hong
    Fu, Lin-An
    Lv, Hao
    Guo, Kun
    Zhu, Hong-Bo
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (03) : 498 - 501
  • [38] Copper-Catalyzed C-C Bond Cleavage/Double Cyclization of α-Ketoamides with o-Phenylene Diamines: Synthesis of Benzimidazo[1,2-c]quinazolin-6-ones
    Zou, Liang-Hua
    Yan, Cheng
    Shi, Kai
    Su, Liang
    Zhu, Shuai
    Jia, Zhe-Kang
    Wang, Qiuan
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (47) : 7725 - 7729
  • [39] Copper-catalyzed gem-difluoromethylenation of C(sp2)-H bonds of alkenes
    Xu, Hui
    Wang, Dejing
    Chen, Yunrong
    Wan, Wen
    Deng, Hongmei
    Ma, Kesen
    Wu, Shaoxiong
    Hao, Jian
    Jiang, Haizhen
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (07): : 1239 - 1243
  • [40] Copper-Catalyzed Arylation of Remote C(sp3)-H Bonds in Carboxamides and Sulfonamides
    Li, Zhaodong
    Wang, Qian
    Zhu, Jieping
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (40) : 13288 - 13292