Construction of a-Halogenated Boronic Esters via Visible Light-Induced C-H Bromination

被引:10
|
作者
Gao, Feng-Chen [1 ]
Li, Ming [1 ]
Gu, Heng-Yu [1 ]
Chen, Xin-Yi [1 ]
Xu, Shuang [1 ]
Wei, Yi [1 ]
Hong, Kai [1 ,2 ]
机构
[1] East China Normal Univ, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, Sch Chem & Mol Engn, Shanghai 200062, Peoples R China
[2] East China Normal Univ, Shanghai Frontiers Sci Ctr Mol Intelligent Synth, Sch Chem & Mol Engn, Shanghai 200062, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 19期
关键词
CATALYZED BORYLATION; ASYMMETRIC-SYNTHESIS; HYDROGENATION; HOMOLOGATION; HALIDES; ACIDS; MECHANISM; SECONDARY; ADDITIONS; ACCESS;
D O I
10.1021/acs.joc.3c01915
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
a-Halogenated boronic esters are versatile building blocks that can be diversified into a wide variety of polyfunctionalized molecules. However, their synthetic potential has been hampered by limited preparation methods. Herein, we report a visible light-induced C-H bromination reaction of readily available benzyl boronic esters. This method features high yields, mild conditions, simple operation, and good functional group tolerance. The analogous chlorides and iodides can be accessed via Finkelstein reaction. Synthesis of halogenated geminal diborons has also been demonstrated.
引用
收藏
页码:14246 / 14254
页数:9
相关论文
共 50 条
  • [1] Visible Light-Induced C-H Alkylation of Azauracils with N-Hydroxyphthalimide Esters via Catalytic EDA Complex
    Zhu, Zhi-Qiang
    Zhang, Wen-Yi
    Huang, Xiao-Long
    Li, Qing
    Xu, Zhen-Zhen
    Rao, Huo-Yu
    JOURNAL OF ORGANIC CHEMISTRY, 2025, 90 (08): : 2842 - 2847
  • [2] Visible light-induced direct α C-H functionalization of alcohols
    Niu, Linbin
    Liu, Jiamei
    Liang, Xing-An
    Wang, Shengchun
    Lei, Aiwen
    NATURE COMMUNICATIONS, 2019, 10 (1)
  • [3] Visible Light-Induced Green Synthesis of Phenanthridines via C-H Activation of Simple Alkanes
    Li, Wenyi
    He, Weimin
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (11) : 4528 - 4530
  • [4] Visible light-induced C-H sulfenylation using sulfinic acids
    Sun, Pengfei
    Yang, Daoshan
    Wei, Wei
    Jiang, Min
    Wang, Zuli
    Zhang, Liyan
    Zhang, Hui
    Zhang, Zhenzhen
    Wang, Yu
    Wang, Hua
    GREEN CHEMISTRY, 2017, 19 (20) : 4785 - 4791
  • [5] Visible Light-Induced C-H Bond Functionalization: A Critical Review
    Revathi, Lekkala
    Ravindar, Lekkala
    Fang, Wan-Yin
    Rakesh, K. P.
    Qin, Hua-Li
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (24) : 4652 - 4698
  • [6] Visible- Light-Induced Direct a C-H Functionalization of Alcohols
    Niu, Linbin
    Liu, Jiamei
    Wang, Shengchun
    Liang, Xing-An
    Lei, Aiwen
    SYNTHESIS-STUTTGART, 2019, 51 (13): : A99 - A101
  • [7] Visible Light-Induced Copper-Catalyzed C-H Arylation of Benzoxazoles
    Ma, Xiaodong
    Zhang, Guozhu
    CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (11) : 1299 - 1303
  • [8] Visible light-induced photocatalytic C-H ethoxycarbonylmethylation of imidazoheterocycles with ethyl diazoacetate
    Bhattacharjee, Suvam
    Laru, Sudip
    Samanta, Sadhanendu
    Singsardar, Mukta
    Hajra, Alakananda
    RSC ADVANCES, 2020, 10 (47) : 27984 - 27988
  • [9] Bis-Cycloruthenated Complexes in Visible Light-Induced C-H Alkylation with Epoxides
    Bentley, Kurt
    Hareram, Mishra Deepak
    Wang, Gang-Wei
    Millman, Alexander A. V.
    Perez-Ortega, Ignacio
    Nichols, Luke M.
    Bories, Cassandre C.
    Walker, Lauren E.
    Woodward, Adam W.
    Golovanov, Alexander P.
    Natrajan, Louise S.
    Larrosa, Igor
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2025, : 5035 - 5042
  • [10] Visible-Light-Induced C-H Cyanoalkylation of Azauracils with Cycloketone Oxime Esters via Catalytic EDA Complex
    Huang, Xiao-Long
    Zhang, Dong-Liang
    Li, Qing
    Xie, Zong-Bo
    Le, Zhang-Gao
    Zhu, Zhi-Qiang
    ORGANIC LETTERS, 2024, 26 (18) : 3727 - 3732