Visible Light-Initiated C(sp3)Br/C(sp3)H Functionalization of -Carbonyl Alkyl Bromides through Hydride Radical Shift

被引:69
|
作者
Li, Yang [1 ]
Liu, Bang [1 ]
Song, Ren-Jie [1 ]
Wang, Qiu-An [1 ]
Li, Jin-Heng [1 ,2 ]
机构
[1] Hunan Univ, Coll Chem & Chem Engn, State Key Lab Chemo Biosensing & Chemometr, Changsha 410082, Peoples R China
[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
关键词
alkyl bromides; enynes; hydride radical shift; polycyclic hydrocarbons; visible light; C-H FUNCTIONALIZATION; CROSS-COUPLING REACTIONS; PHOTOREDOX CATALYSIS; ELECTRON-TRANSFER; BOND FUNCTIONALIZATION; CYCLIZATION APPROACH; MEDIATED SYNTHESIS; ONE-POT; TRIFLUOROMETHYLATION; ALKENES;
D O I
10.1002/adsc.201501134
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A new visible light- initiated 1,5- hydride radical shift strategy has been developed to enable the one- step functionalization of both a C( sp3) Br bond and a C(sp3) H bond adjacent to the same carbon atom. This visible light photoredox catalysis offers a mild and straightforward access to diverse five- membered carbocyclic ring- fused polycyclic hydrocarbons with high turnover numbers (TONs; up to 4.93 x 103) and broad substrate scope.
引用
收藏
页码:1219 / 1228
页数:10
相关论文
共 50 条
  • [21] Visible-Light-Promoted Site-Specific and Diverse Functionalization of a C(sp3)-C(sp3) Bond Adjacent to an Arene
    Wang, Yaxin
    Wang, Nengyong
    Zhao, Jianyou
    Sun, Minzhi
    You, Huichao
    Fang, Fang
    Liu, Zhong-Quan
    ACS CATALYSIS, 2020, 10 (12): : 6603 - 6612
  • [22] Visible light promoted photoredox C(sp3)-H bond functionalization of tetrahydroisoquinolines in flow
    Filipovic, Ana
    Dzambaski, Zdravko
    Vasiljevic-Radovic, Dana
    Bondzic, Bojan P.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (12) : 2668 - 2675
  • [23] Visible-Light-Driven α-C(sp3)-H Bond Functionalization of Glycine Derivatives
    Tian, Yao
    Bu, Xiubin
    Chen, Yuanrui
    Wang, Luohe
    Junnan, E.
    Zeng, Jing
    Xu, Hao
    Han, Aihong
    Yang, Xiaobo
    Zhao, Zhen
    CATALYSTS, 2023, 13 (12)
  • [24] Photochemically Induced Radical Transformation of C(sp3)-H Bonds to C(sp3)-CN Bonds
    Kamijo, Shin
    Hoshikawa, Tamaki
    Inoue, Masayuki
    ORGANIC LETTERS, 2011, 13 (21) : 5928 - 5931
  • [25] Visible-Light-Induced Alkoxyl Radical Generation Enables Selective C(sp3)-C(sp3) Bond Cleavage and Functionalizations
    Jia, Kunfang
    Zhang, Fuyuan
    Huang, Hanchu
    Chen, Yiyun
    Journal of the American Chemical Society, 2016, 138 (05): : 1514 - 1517
  • [26] Visible-Light-Induced Alkoxyl Radical Generation Enables Selective C(sp3)-C(sp3) Bond Cleavage and Functionalizations
    Jia, Kunfang
    Zhang, Fuyuan
    Huang, Hanchu
    Chen, Yiyun
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (05) : 1514 - 1517
  • [27] Radical C(sp3)–H functionalization and cross-coupling reactions
    Dung L. Golden
    Sung-Eun Suh
    Shannon S. Stahl
    Nature Reviews Chemistry, 2022, 6 : 405 - 427
  • [28] Catalytic enantioselective C(sp3)–H functionalization involving radical intermediates
    Chi Zhang
    Zhong-Liang Li
    Qiang-Shuai Gu
    Xin-Yuan Liu
    Nature Communications, 12
  • [29] Catalytic enantioselective C(sp3)-H functionalization involving radical intermediates
    Zhang, Chi
    Li, Zhong-Liang
    Gu, Qiang-Shuai
    Liu, Xin-Yuan
    NATURE COMMUNICATIONS, 2021, 12 (01)
  • [30] Advances in C(sp3)-H Bond Functionalization via Radical Processes
    Zhang, Tong
    Wu, Yue-Hua
    Wang, Nai-Xing
    Xing, Yalan
    SYNTHESIS-STUTTGART, 2019, 51 (24): : 4531 - 4548