O-Perfluoropyridin-4-yl Oximes: Iminyl Radical Precursors for Photo- or Thermal-Induced N-O Cleavage in C(sp2) C(sp3) Bond Formation

被引:37
|
作者
Xia, Peng-Ju [1 ]
Hu, Yuan-Zhuo [1 ]
Ye, Zhi-Peng [1 ]
Li, Xu-Jie [1 ]
Xiang, Hao-Yue [1 ]
Yang, Hua [1 ,2 ]
机构
[1] Cent South Univ, Coll Chem & Chem Engn, Changsha 410083, Peoples R China
[2] Cent South Univ, Key Lab Hunan Prov Water Environm & Agr Prod Safe, Changsha 410083, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 05期
基金
中国国家自然科学基金;
关键词
C-H CYANOALKYLATION; VISIBLE-LIGHT; FACILE ACCESS; QUINOXALIN-2(1H)-ONES; CYCLIZATION; GENERATION; ALKENES; ARYLATION; CATALYSTS; CASCADE;
D O I
10.1021/acs.joc.9b03251
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
O-Perfluoropyridin-4-yl group was first installed onto cycloketone oximes as a new electrophore, which was proven to be efficient iminyl radical precursors under photocatalytic and thermal conditions. A range of O-perfluoropyridin-4-yl oximes were successfully utilized in C(sp(2))-C(sp(3)) bond formations of quinoxalin-2(1H)-ones and alkenes, providing facile accesses to a range of functionalized alkylnitriles.
引用
收藏
页码:3538 / 3547
页数:10
相关论文
共 50 条
  • [11] Crystal structure of 2,6-dimethylpyridinium hydrogen fumarate:: Hydrogen bonds of C(sp3)-H•••O, C(sp2)-H•••O and N+-H••O-(sp3)
    Pan, YJ
    Jin, ZM
    Sun, CR
    Jiang, CW
    CHEMISTRY LETTERS, 2001, (10) : 1008 - 1009
  • [12] Catalytic C(sp2)-C(sp3) Bond Formation of Methoxyarenes by the Organic Superbase t-Bu-P4
    Shigeno, Masanori
    Hayashi, Kazutoshi
    Nozawa-Kumada, Kanako
    Kondo, Yoshinori
    ORGANIC LETTERS, 2020, 22 (22) : 9107 - 9113
  • [13] Copper Promoted Aerobic Oxidative C(sp3)-C(sp3) Bond Cleavage of N-(2-(Pyridin-2-yl)-ethyl)anilines
    Yu, Yang
    Zhang, Yong
    Sun, Chengyu
    Shi, Lei
    Wang, Wei
    Li, Hao
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (04): : 2725 - 2732
  • [14] Photo-Induced Ruthenium-Catalyzed Double Remote C(sp2)-H / C(sp3)-H Functionalizations by Radical Relay
    Wang, Yulei
    Chen, Shan
    Chen, Xinran
    Zangarelli, Agnese
    Ackermann, Lutz
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (32)
  • [15] Palladium-Catalyzed Redox-Neutral N-O/C(sp3)-H Functionalization of Aryl Oximes with lsocyanides
    Hu, Weigao
    Li, Jiawei
    Xu, Yanli
    Li, Jianxiao
    Wu, Wanqing
    Liu, Haiyang
    Jiang, Huanfeng
    ORGANIC LETTERS, 2017, 19 (03) : 678 - 681
  • [16] Palladium-Catalyzed C(sp2 and sp3)-H Activation/C-O Bond Formation: Synthesis of Benzoxaphosphole 1- and 2-Oxides
    Eom, Dahan
    Jeong, Yeonseok
    Kim, Yea Rin
    Lee, Euichul
    Choi, Wonseok
    Lee, Phil Ho
    ORGANIC LETTERS, 2013, 15 (20) : 5210 - 5213
  • [17] Radical addition to the C=C bond meets (1,n)-HAT: recent advances in the remote C(sp3)-H or C(sp2)-H functionalization of alkenes
    Xi, Ji Ming
    Liao, Wei-Wei
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (16) : 4490 - 4506
  • [18] Visible-Light-Induced Radical Cascade Cross-Coupling via C(sp3)-H Activation and C-N/N-O Cleavage: Feasible Access to Methylenebisamide Derivatives
    Lei, Jinglan
    Li, Min
    Zhang, Qingqing
    Liu, Shuyang
    Li, Haifang
    Shi, Lei
    Jiang, Wen-Feng
    Duan, Chunying
    Jin, Yunhe
    ORGANIC LETTERS, 2023, 25 (13) : 2300 - 2305
  • [19] Cobalt-Catalyzed Secondary Alkylation of Arenes and Olefins with Alkyl Ethers through the Cleavage of C(sp2)-H and C(sp3)-O Bonds
    Dong, Xunqing
    Li, Qun
    Li, Guigen
    Lu, Hongjian
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (21): : 13402 - 13413
  • [20] STEREOCHEMISTRY OF THE C(SP2)-N(SP3) FRAGMENT .2. STRUCTURE OF (E)-N,N'-DICYCLOHEXYL-4-MORPHOLINECARBOXAMIDINE, C17H31N3O
    BELLUCCI, F
    BERTOLASI, V
    FERRETTI, V
    GILLI, G
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1985, 41 (APR) : 544 - 546