Photocatalyst-Free Transformation of C(sp3)-H Bonds to Oxime Ethers via Photoinduced Hydrogen Atom Transfer

被引：0
|
作者：
Zhao, Yu-Lian [1 ,2 ]
Min, Xuehong [3 ]
Li, Lijing [1 ,2 ]
Han, Xiao-Le [1 ,2 ]
Wei, Yi [1 ,2 ]
Hu, Xiao-Qiang [1 ,2 ]
机构：
[1] South Cent Minzu Univ, Sch Chem & Mat Sci, Key Lab Catalysis & Energy Mat Chem, Minist Educ, Wuhan 430074, Peoples R China
[2] South Cent Minzu Univ, Sch Chem & Mat Sci, Hubei Key Lab Catalysis & Mat Sci, Wuhan 430074, Peoples R China
[3] Wuhan Business Univ, Hubei Prov Engn Res Ctr Racing Horse Detect & Appl, Equine Sci Res & Horse Doping Control Lab, Wuhan 430056, Peoples R China
来源：
ORGANIC LETTERS | 2024年 / 26卷 / 43期
基金：
中国国家自然科学基金;
关键词：
FUNCTIONAL-GROUP; SINGLET OXYGEN; ACTIVATION; AZIDE;
D O I：
10.1021/acs.orglett.4c03653
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, a direct transformation of aliphatic C-H bonds to oxime ethers has been developed via light-promoted hydrogen atom transfer (HAT) in the absence of a photocatalyst. Singlet oxygen and chlorine radical are complementary C(sp(3))-H bond cleaving agents in this reaction, enabling the extraction of hydrogen atoms from a diverse range of compounds, like cycloalkanes, ethers, amines, amides, and cyclic sulfides. This method excels in transforming common aliphatic C-H bonds into valuable oxime ethers featuring abundant chemical feedstocks, good functional group tolerance, and catalyst free conditions.
引用
收藏
页码：9383 / 9388
页数：6
相关论文
共 50 条
  • [41] β-Arylation of oxime ethers using diaryliodonium salts through activation of inert C(sp3)-H bonds using a palladium catalyst
    Peng, Jing
    Chen, Chao
    Xi, Chanjuan
    CHEMICAL SCIENCE, 2016, 7 (02) : 1383 - 1387
  • [42] Co-Catalyzed C(sp3)-C(sp2) bond cleavage via hydrogen atom transfer
    Zhou, Bingqing
    Tian, Di
    An, Jinglin
    Zhou, Yalan
    Yan, Rui
    Song, Hao
    Liu, Xiao-Yu
    Qin, Yong
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (08) : 2135 - 2140
  • [43] Electrochemical and Scalable Dehydrogenative C(sp3)-H Amination via Remote Hydrogen Atom Transfer in Batch and Continuous Flow
    Nikolaienko, Pavlo
    Jentsch, Marc
    Kale, Ajit P.
    Cai, Yunfei
    Rueping, Magnus
    CHEMISTRY-A EUROPEAN JOURNAL, 2019, 25 (29) : 7177 - 7184
  • [44] Metal-free photoinduced C(sp3)-H borylation of alkanes
    Shu, Chao
    Noble, Adam
    Aggarwal, Varinder K.
    NATURE, 2020, 586 (7831) : 714 - 719
  • [45] Metal-free photoinduced C(sp3)–H borylation of alkanes
    Chao Shu
    Adam Noble
    Varinder K. Aggarwal
    Nature, 2020, 586 : 714 - 719
  • [46] Metal-free, photoinduced remote C(sp3)-H borylation
    He, Jiachen
    Cook, Silas P.
    CHEMICAL SCIENCE, 2023, 14 (35) : 9476 - 9481
  • [47] Hypervalent-iodine promoted selective cleavage of C(sp3)-C(sp3) bonds in ethers
    Wang, Yaxin
    He, Qin
    Cao, Zehui
    Wang, Peng
    Chen, Gong
    Beller, Matthias
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (20): : 5592 - 5598
  • [48] Metallaphotoredox catalysis for sp3 C-H functionalizations through hydrogen atom transfer (HAT)
    Zhang, Jingchang
    Rueping, Magnus
    CHEMICAL SOCIETY REVIEWS, 2023, 52 (12) : 4099 - 4120
  • [49] Transition-Metal-Free C(sp3)-H Coupling of Cycloalkanes Enabled by Single-Electron Transfer and Hydrogen Atom Transfer
    Zhang, Linlin
    Liu, Zhengfen
    Tian, Xun
    Zi, Yujin
    Duan, Shengzu
    Fang, Yongsheng
    Chen, Wen
    Jing, Hong
    Yang, Lijuan
    Yang, Xiaodong
    ORGANIC LETTERS, 2021, 23 (05) : 1714 - 1719
  • [50] Intramolecular Hydrogen Atom Transfer from Unactivated C(sp3)-H Bond to Alkyl Radical
    Liu, Huiying
    Jin, Qihao
    Wu, Xinxin
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (08)
12345