Iron(II)-catalyzed direct C-H cyanoalkylation of 2H-indazoles and coumarins via radical C-C bond cleavage

被引：20
|
作者：
Gao, Pin [1 ]
Cheng, Yuan-Bo [1 ]
Yang, Fan [1 ]
Guo, Li-Na [1 ]
Duan, Xin-Hua [1 ]
机构：
[1] Xi An Jiao Tong Univ, MOE Key Lab Nonequilibrium Synth & Modulat Conden, Xian Key Lab Sustainable Energy Mat Chem, Dept Chem,Sch Sci, Xian 710049, Shaanxi, Peoples R China
来源：
TETRAHEDRON LETTERS | 2019年 / 60卷 / 35期
基金：
中国博士后科学基金;
关键词：
Iron; Cyanoalkylation; Heterocycles; Radical; REGIOSELECTIVE SYNTHESIS; RING-CLEAVAGE; OXIME ESTERS; FUNCTIONALIZATION; INHIBITORS; FLAVONES; ACCESS; ETHERS; ACIDS;
D O I：
10.1016/j.tetlet.2019.150967
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An iron-catalyzed C-3 cyanoalkylation of 2H-indazole and coumarin derivates with cyclobutanone oxime esters has been accomplished, which proceeds efficiently in a high regioselective manner to construct diverse alkylated 2H-indazole and coumarin derivates in moderate to good yields. Preliminary mechanistic studies reveal that a distal cyanosubstituted alkyl radicals intermediate would be formed through radical-involved C-C bond cleavage of cyclobutanone oximes ester. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页数：4
相关论文
共 50 条
  • [21] Palladium(II)-Catalyzed C-H Bond Activation/C-C and C-O Bond Formation Reaction Cascade: Direct Synthesis of Coumestans
    Neog, Kashmiri
    Borah, Ashwini
    Gogoi, Pranjal
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (23) : 11971 - 11977
  • [22] Rh(iii)-Catalyzed acylation of heteroarenes with cyclobutenones via C-H/C-C bond activation
    Cui, Yixin
    Bai, Dachang
    Liu, Bingxian
    Chang, Junbiao
    Li, Xingwei
    CHEMICAL COMMUNICATIONS, 2020, 56 (100) : 15631 - 15634
  • [23] Recent advances in radical-mediated fluorination through C-H and C-C bond cleavage
    Hong Yan
    Chen Zhu
    Science China(Chemistry), 2017, (02) : 214 - 222
  • [24] Recent advances in radical-mediated fluorination through C-H and C-C bond cleavage
    Yan, Hong
    Zhu, Chen
    SCIENCE CHINA-CHEMISTRY, 2017, 60 (02) : 214 - 222
  • [25] Minisci-Type C-H Cyanoalkylation of Heteroarenes Through N-O/C-C Bonds Cleavage
    Jian, Yong
    Chen, Ming
    Yang, Chao
    Xia, Wu-jiong
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (10) : 1439 - 1442
  • [26] Photoredox-catalyzed regio- & stereoselective C(sp2)-H cyanoalkylation of enamides with cycloketone oximes via selective C-C bond cleavage/radical addition cascade
    Guan, Ting
    Guo, Jing-Yu
    Zhang, Qing-Hong
    Xu, Xin-Wen
    Yu, Xiao-Yu
    Zhang, Yu
    Zhao, Kai
    GREEN CHEMISTRY, 2022, 24 (17) : 6524 - 6530
  • [27] Benzylic C-H heteroarylation of 4-Methylphenols with 2H-Indazoles
    Yuan, Cheng
    Chen, Dongdong
    Pan, Changduo
    Yu, Jin-Tao
    TETRAHEDRON LETTERS, 2022, 105
  • [28] Synthesis of 1,4-Naphthoquinones via Palladium(II)-Catalyzed Tertiary C-H Alkylation of Olefins Followed by C-C Bond Cleavage
    Zhang, Xu
    Chang, Mengfan
    Ni, Tongtong
    Xu, Xuefeng
    Li, Wenguang
    Li, Ting
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2025, 28 (04)
  • [29] Palladium-Catalyzed Direct Alkoxycarbonylation of Aromatic C-H Bonds via Selective C-C Cleavage of α-Keto Esters
    Zhou, Wei
    Li, Pinhua
    Zhang, Yicheng
    Wang, Lei
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (11-12) : 2343 - 2352
  • [30] Copper-mediated C-H amination of 2H-indazoles with N-Fluorobenzenesulfonimide
    Li, Zhenhua
    Ye, Lixian
    Cao, Yingyan
    Qin, Jinjing
    Wang, Wenbiao
    Xie, Yuanyuan
    TETRAHEDRON LETTERS, 2021, 83
12345