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
  • [1] Direct C-H Cyanoalkylation of Quinoxalin-2(1H)-ones via Radical C-C Bond Cleavage
    Yang, Lin
    Gao, Pin
    Duan, Xin-Hua
    Gu, Yu-Rui
    Guo, Li-Na
    ORGANIC LETTERS, 2018, 20 (04) : 1034 - 1037
  • [2] Direct C-H Cyanoalkylation of Heteroaromatic N-Oxides and Quinones via C-C Bond Cleavage of Cyclobutanone Oximes
    Gu, Yu-Rui
    Duan, Xin-Hua
    Yang, Lin
    Guo, Li-Na
    ORGANIC LETTERS, 2017, 19 (21) : 5908 - 5911
  • [3] Transition-Metal-Promoted Direct C-H Cyanoalkylation and Cyanoalkoxylation of Internal Alkenes via Radical C-C Bond Cleavage of Cycloketone Oxime Esters
    Lou, Jiang
    He, Yuan
    Li, Yunlong
    Yu, Zhengkun
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (16) : 3787 - 3799
  • [4] Ru(II)-Catalyzed Tunable Cascade Reaction via C-H/C-C Bond Cleavage
    Yang, Zi
    Yue, Qi
    Yang, Mengqi
    Zhang, Hong
    Cui, Xiuling
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (20) : 12960 - 12970
  • [5] Rh(III)-catalyzed C-H acylmethylation of 2H-indazoles with sulfoxonium ylides
    Wang, Ya-Gai
    Li, Jing
    Wang, Xiao-Die
    Shi, Linlin
    Zhu, Xinju
    Hao, Xin-Qi
    Song, Mao-Ping
    JOURNAL OF SAUDI CHEMICAL SOCIETY, 2020, 24 (11) : 850 - 856
  • [6] C-H Cyanoalkylation:the direct C-H Cyanomethylation of Naphthalimide
    Chen, Xi
    Li, Zheyao
    Chen, Yayun
    Chen, Zhihua
    Hu, Yan
    Liu, Chuanxiang
    PROGRESS IN CHEMISTRY, 2021, 33 (11) : 1947 - 1952
  • [7] Iron-Catalyzed π-Activated C-O Ether Bond Cleavage with C-C and C-H Bond Formation
    Fan, Xiaohui
    Cui, Xiao-Meng
    Guan, Yong-Hong
    Fu, Lin-An
    Lv, Hao
    Guo, Kun
    Zhu, Hong-Bo
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (03) : 498 - 501
  • [8] Iron-catalyzed C-C bond formation by direct functionalization of C-H bonds adjacent to heteroatoms
    Li, Zhiping
    Yu, Rong
    Li, Haijun
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (39) : 7497 - 7500
  • [9] Iron-Catalyzed C-C Bond Formation via Chelation-Assisted C-H Activation
    Yoshikai, Naohiko
    ISRAEL JOURNAL OF CHEMISTRY, 2017, 57 (12) : 1117 - 1130
  • [10] Rh(III)-Catalyzed Double C-H Functionalization of Indoles with Cyclopropenones via Sequential C-H/C-C/C-H Bond Activation
    Zhang, Yan-Bo
    Li, Bin-Shi
    Xu, Guo-Jie
    Sun, Wei
    Sun, Meng
    ORGANIC LETTERS, 2023, 25 (21) : 3922 - 3926
12345