Copper-catalyzed C-3 benzylation of quinoxalin-2(1H)-ones with benzylsulfonyl hydrazides

被引:8
作者
Xie, Dong
Tian, Ren-Gui
Zhang, Xue-Ting
Tian, Shi-Kai [1 ]
机构
[1] Univ Sci & Technol China, Hefei Natl Res Ctr Phys Sci Microscale, Hefei 230026, Anhui, Peoples R China
基金
中国国家自然科学基金;
关键词
DECARBOXYLATIVE ACYLATION; ARYLSULFONYL HYDRAZIDES; SULFONYL HYDRAZIDES; METAL; ARYLATION; TOSYLHYDRAZONES; DERIVATIVES; REAGENTS;
D O I
10.1039/d2ob00744d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An unprecedented use of benzylsulfonyl hydrazides as benzylating agents has been demonstrated in the direct C-3 benzylation of quinoxalin-2(1H)-ones. A range of benzylsulfonyl hydrazides participated in the C-3 benzylation of quinoxalin-2(1H)-ones with CuCN as the catalyst and DTBP as the oxidant, delivering structurally diverse 3-benzylquinoxalin-2(1H)-ones in moderate to good yields.
引用
收藏
页码:4518 / 4521
页数:4
相关论文
共 49 条
  • [1] RECENT APPLICATIONS OF THE SHAPIRO REACTION
    ADLINGTON, RM
    BARRETT, AGM
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1983, 16 (02) : 55 - 59
  • [2] Visible-light-induced C-H arylation of quinoxalin-2(1H)-ones in H2O
    Bao, Hanyang
    Lin, Ziyun
    Jin, Mengshi
    Zhang, Hongdou
    Xu, Jun
    Chen, Bajin
    Li, Wanmei
    [J]. TETRAHEDRON LETTERS, 2021, 66
  • [3] Tosylhydrazones: New Uses for Classic Reagents in Palladium-Catalyzed Cross-Coupling and Metal-Free Reactions
    Barluenga, Jose
    Valdes, Carlos
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (33) : 7486 - 7500
  • [4] Palladium(II)-Catalyzed Oxidative Arylation of Quinoxalin-2(1H)-ones with Arylboronic Acids
    Carrer, Amandine
    Brion, Jean-Daniel
    Messaoudi, Samir
    Alami, Mouad
    [J]. ORGANIC LETTERS, 2013, 15 (21) : 5606 - 5609
  • [5] Alkyl Carbazates for Electrochemical Deoxygenative Functionalization of Heteroarenes
    Gao, Yongyuan
    Wu, Zhengguang
    Yu, Lei
    Wang, Yi
    Pan, Yi
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (27) : 10859 - 10863
  • [6] TfNHNHBoc as a Trifluoromethylating Agent for Vicinal Difunctionalization of Terminal Alkenes
    Guo, Jing-Yu
    Wu, Ruo-Xin
    Jin, Ji-Kang
    Tian, Shi-Kai
    [J]. ORGANIC LETTERS, 2016, 18 (15) : 3850 - 3853
  • [7] BI-OAc-Accelerated C3-H Alkylation of Quinoxalin-2(1H)-ones under Visible-Light Irradiation
    He, Xiang-Kui
    Lu, Juan
    Zhang, Ai-Jun
    Zhang, Qing-Qing
    Xu, Guo-Yong
    Xuan, Jun
    [J]. ORGANIC LETTERS, 2020, 22 (15) : 5984 - 5989
  • [8] Copper-Catalyzed Direct C-3 Benzylation of Quinoxalin-2(1H)-ones with Methylarenes under Microwave Irradiation
    Hu, Leqian
    Yuan, Jinwei
    Fu, Junhao
    Zhang, Taotao
    Gao, Lele
    Xiao, Yongmei
    Mao, Pu
    Qu, Lingbo
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (30) : 4113 - 4120
  • [9] Aerobic Oxidative Coupling between Carbon Nucleophiles and Allylic Alcohols: A Strategy to Construct β-(Hetero)Aryl Ketones and Aldehydes through Hydrogen Migration
    Huang, Liangbin
    Qi, Ji
    Wu, Xia
    Wu, Wanqing
    Jiang, Huanfeng
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (46) : 15462 - 15466
  • [10] Electrochemical Cross-Coupling of C(sp2)-H with Aryldiazonium Salts via a Paired Electrolysis: an Alternative to Visible Light Photoredox-Based Approach
    Jiang, Yang-ye
    Dou, Gui-yuan
    Zhang, Luo-sha
    Xu, Kun
    Little, R. Daniel
    Zeng, Cheng-chu
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (22) : 5170 - 5175