Direct Synthesis of Disubstituted 3-Isoquinolinone Derivatives through the Construction of C-N, C=O, and C(sp2)-C(sp3) Bonds under Transition-Metal-Free Conditions

被引:11
|
作者
Shi, Jianyi [1 ]
Chen, Xia [1 ]
Huang, Jingyun [1 ]
Lu, Yantong [1 ]
Yang, Zhendong [1 ]
Zhong, Mingli [2 ]
Zhu, Zhongzhi [1 ]
Chen, Xiuwen [1 ]
机构
[1] Wuyi Univ, Sch Biotechnol & Hlth Sci, Jiangmen 529020, Peoples R China
[2] Guilin Med Univ, Pharmacol Lab Prevent & Treatment High Incidence D, Guilin 541199, Peoples R China
基金
中国国家自然科学基金;
关键词
acetophenone; dearomatization; nitromethane; trifunctionalization; CATALYZED HYDROXYLATION; EFFICIENT SYNTHESIS; ARYL HALIDES; FUNCTIONALIZATION; ISOQUINOLINES; OXIDATION; PHENOLS;
D O I
10.1002/ejoc.202201231
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The efficient three-component cascade coupling reaction of 3-haloisoquinolines, haloalkanes, and sp(3)-carbon nucleophiles (acetophenone or nitromethane) led to a series of structurally novel 1,2-disubstituted-3-isoquinolinones through the formation of C(sp(3))-C(sp(2)), C-N, and C=O bonds. The NaOAc-promoted reaction described in this work is simple to operate, environment friendly, and highly selective.
引用
收藏
页数:5
相关论文
共 50 条
  • [21] A convenient and versatile SNAr-decarboxylation protocol for the construction of C(sp2)-C(sp3) bonds
    Burtea, Alexander
    DeForest, Jacob
    Baldwin, Neil
    Leverett, Carolyn
    Gallego, Gary M.
    CHEMICAL COMMUNICATIONS, 2022, 58 (53) : 7435 - 7438
  • [22] Transition-Metal-Free Intermolecular Amination of sp3 C-H Bonds with Sulfonamides
    Fan, Renhua
    Li, Weixun
    Pu, Dongming
    Zhang, Li
    ORGANIC LETTERS, 2009, 11 (06) : 1425 - 1428
  • [23] Redox-Activated Amines in C(sp3)-C(sp) and C(sp3)-C(sp2) Bond Formation Enabled by Metal-Free Photoredox Catalysis
    Ociepa, Michal
    Turkowska, Joanna
    Gryko, Dorota
    ACS CATALYSIS, 2018, 8 (12): : 11362 - 11367
  • [24] Transition metal mediated activation of C(sp3)-C(sp2) bond in aromatic hydrocarbons
    Yan, Nai-He
    Luo, HuaIi
    SYNTHETIC COMMUNICATIONS, 2022, 52 (02) : 157 - 174
  • [25] Transition-Metal-Free Deacylative Cleavage of Unstrained C(sp3)-C(sp2) Bonds: Cyanide-Free Access to Aryl and Aliphatic Nitriles from Ketones and Aldehydes
    Ge, Jing-Jie
    Yao, Chuan-Zhi
    Wang, Mei-Mei
    Zheng, Hong-Xing
    Kang, Yan-Biao
    Li, Yadong
    ORGANIC LETTERS, 2016, 18 (02) : 228 - 231
  • [26] Enantioselective C(sp2)-C(sp3) Bond Construction by Ni Catalysis
    Chen, Li-Ming
    Reisman, Sarah E.
    ACCOUNTS OF CHEMICAL RESEARCH, 2024, 57 (05) : 751 - 762
  • [27] Tuneable access to isoquinolines via a transition-metal-free C(sp3)-C(sp3) bond cleavage rearrangement reaction
    Wang, Jian
    Cai, Panyuan
    He, Yimiao
    Liu, Yuan
    Zhong, Ling
    Ding, Shumin
    Shang, Yongjia
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (14) : 2430 - 2434
  • [28] Coupling of C(sp3)-H bonds with C(sp2)-O electrophiles: mild, general and selective
    Gui, Yong-Yuan
    Liao, Li-Li
    Sun, Liang
    Zhang, Zhen
    Ye, Jian-Heng
    Shen, Guo
    Lu, Zhi-Peng
    Zhou, Wen-Jun
    Yu, Da-Gang
    CHEMICAL COMMUNICATIONS, 2017, 53 (06) : 1192 - 1195
  • [29] Preparation of Alkyl Di(p-tolyl)sulfonium Salts and Their Application in Metal-Free C(sp3)-C(sp3) and C(sp3)-C(sp2) Bond Formations
    Higuchi, Kazuhiro
    Yamamoto, Kai
    Nakamura, Shunsuke
    Naruse, Haruka
    Ito, Motoki
    Sugiyama, Shigeo
    ORGANIC LETTERS, 2023, 25 (20) : 3766 - 3771
  • [30] An Articulate Oxidative Transition-Metal-Free Homocoupling of Imidazo Heterocycles through C(sp2)-C(sp2) Bond Formation
    Shakoor, S. M. Abdul
    Mandal, Sanjay K.
    Sakhuja, Rajeev
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (18) : 2596 - 2602