Rh(III)-catalyzed C8 arylation of quinoline N-oxides with arylboronic acids

被引：9
作者：
Huang, Yuanqiong [1 ]
Lv, Xueli [1 ]
Song, Hongjian [1 ]
Liu, Yuxiu [1 ]
Wang, Qingmin [1 ,2 ]
机构：
[1] Nankai Univ, Res Inst Elementoorgan Chem, Coll Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
[2] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China
来源：
CHINESE CHEMICAL LETTERS | 2020年 / 31卷 / 06期
基金：
中国国家自然科学基金;
关键词：
Rh-III-catalyzed; C8; arylation; Quinoline N-oxides; Arylboronic acids; Regioselectivity; H BOND ACTIVATION; ASYMMETRIC-SYNTHESIS; CATALYZED ARYLATION; C-8; POSITION; MILD; METAL; ALKENYLATION; C(SP(3))-H; ALKENES; ARYL;
D O I：
10.1016/j.cclet.2019.11.028
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Herein, we report the first Rh-III-catalyzed regioselective C8 arylation of quinoline N-oxides with commercially available arylboronic acids as coupling partners. This procedure is simple, and the reaction shows perfect regioselectivity, a broad substrate scope, and isolated yields of up to 92%. We demonstrate the utility of the reaction by using it for late-stage functionalization of a fungicide. (c) 2019 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：1572 / 1575
页数：4
相关论文
共 74 条
  • [1] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope
    Ackermann, Lutz
    [J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1315 - 1345
  • [2] Cobalt(III) catalyzed C-8 selective C-H and C-O coupling of quinoline N-oxide with internal alkynes via C-H activation and oxygen atom transfer
    Barsu, Nagaraju
    Sen, Malay
    Premkumar, J. Richard
    Sundararaju, Basker
    [J]. CHEMICAL COMMUNICATIONS, 2016, 52 (07) : 1338 - 1341
  • [3] Bergman RG, 2007, NATURE, V446, P391, DOI 10.1038/446391a
  • [4] Burgin A.B., 2011, CURR MED CHEM, V18, P1433
  • [5] Palladium-Catalyzed Direct Arylation of Azine and Azole N-Oxides: Reaction Development, Scope and Applications in Synthesis
    Campeau, Louis-Charles
    Stuart, David R.
    Leclerc, Jean-Philippe
    Bertrand-Laperle, Megan
    Villemure, Elisia
    Sun, Ho-Yan
    Lasserre, Sandrine
    Guimond, Nicolas
    Lecavallier, Melanie
    Fagnou, Keith
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (09) : 3291 - 3306
  • [6] C8-Selective Acylation of Quinoline N-Oxides with α-Oxocarboxylic Acids via Palladium-Catalyzed Regioselective C-H Bond Activation
    Chen, Xiaopei
    Cui, Xiuling
    Wu, Yangjie
    [J]. ORGANIC LETTERS, 2016, 18 (15) : 3722 - 3725
  • [7] "One-Pot" Approach to 8-Acylated 2-Quinolinones via Palladium-Catalyzed Regioselective Acylation of Quinoline N-Oxides
    Chen, Xiaopei
    Cui, Xiuling
    Wu, Yangjie
    [J]. ORGANIC LETTERS, 2016, 18 (10) : 2411 - 2414
  • [8] Base-Promoted Cross-Dehydrogenative Coupling of Quinoline N-Oxides with 1,3-Azoles
    Chen, Xiaopei
    Cui, Xiuling
    Yang, Fangfang
    Wu, Yangjie
    [J]. ORGANIC LETTERS, 2015, 17 (06) : 1445 - 1448
  • [9] Direct 2-acetoxylation of quinoline N-oxides via copper catalyzed C-H bond activation
    Chen, Xuan
    Zhu, Chongwei
    Cui, Xiuling
    Wu, Yangjie
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (61) : 6900 - 6902
  • [10] Palladium-catalyzed C-H functionalization of pyridine N-oxides:: Highly selective alkenylation and direct arylation with unactivated arenes
    Cho, Seung Hwan
    Hwang, Seung Jun
    Chang, Sukbok
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) : 9254 - +
12345678