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
  • [21] Factors That Control C-C Cleavage versus C-H Bond Hydroxylation in Copper-Catalyzed Oxidations of Ketones with O2
    Tsang, Althea S. -K.
    Kapat, Ajoy
    Schoenebeck, Franziska
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (02) : 518 - 526
  • [22] Copper-Catalyzed Aerobic Oxidative C-C Bond Cleavage for C-N Bond Formation: From Ketones to Amides
    Tang, Conghui
    Jiao, Ning
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (25) : 6528 - 6532
  • [23] Copper-Catalyzed Aerobic Dehydrogenation of C-C to C=C Bonds in the Synthesis of Pyridazinones
    Liang, Lei
    Yang, Guanyu
    Xu, Fengrong
    Niu, Yan
    Sun, Qi
    Xu, Ping
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (27) : 6130 - 6136
  • [24] Copper-Catalyzed Cascade Transformation of Homopropargyl Azides into Trifluoromethylated Nitriles via C-C Cleavage
    Chen, Shuang
    Li, Deng-Yuan
    Jiang, Liang-Liang
    Liu, Kai
    Liu, Pei-Nian
    ORGANIC LETTERS, 2017, 19 (08) : 2014 - 2017
  • [25] Copper-Catalyzed Direct Arylselenation of Anilines by C-H Bond Cleavage
    Ricordi, Vanessa G.
    Thurow, Samuel
    Penteado, Filipe
    Schumacher, Ricardo F.
    Perin, Gelson
    Lenardao, Eder J.
    Alves, Diego
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (05) : 933 - 939
  • [26] COPPER-CATALYZED C-C BOND FORMATION OF ZIRCONACYCLES AND ITS APPLICATION
    TAKAHASHI, T
    KOTORA, M
    KASAI, K
    SUZUKI, N
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 208 : 65 - ORGN
  • [27] Asymmetric formal C-C bond insertion into aldehydes via copper-catalyzed diyne cyclization
    Li, Cui-Ting
    Qi, Lin-Jun
    Liu, Li-Gao
    Ge, Chang
    Lu, Xin
    Ye, Long-Wu
    Zhou, Bo
    NATURE COMMUNICATIONS, 2023, 14 (01)
  • [28] Recent Progress on Copper-Catalyzed C-C Bond Formation via C(sp 2 )-H Insertions Using Diazo and Related Compounds
    Bera, Satabdi
    Jana, Subhenira
    Samanta, Rajarshi
    SYNTHESIS-STUTTGART, 2024, 56 (01): : 29 - 46
  • [29] Copper-catalyzed aerobic oxidative cleavage of C-C bonds in epoxides leading to aryl nitriles and aryl aldehydes
    Gu, Lijun
    Jin, Cheng
    CHEMICAL COMMUNICATIONS, 2015, 51 (30) : 6572 - 6575
  • [30] Copper-catalyzed redox-neutral C-H amination with amidoximes
    Chen, Hui
    Chiba, Shunsuke
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (01) : 42 - 46