Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Phosphates with Aryl Bromides

被引:18
|
作者
Ren, Jing-Ao [1 ]
Chen, Xue [1 ]
Gui, Chao [1 ]
Miao, Chengping [2 ]
Chu, Xue-Qiang [1 ]
Xu, Hao [1 ]
Zhou, Xiaocong [1 ,2 ]
Ma, Mengtao [3 ]
Shen, Zhi-Liang [1 ]
机构
[1] Nanjing Tech Univ, Tech Inst Fluorochem TIF, Inst Adv Synth, Sch Chem & Mol Engn, Nanjing 211816, Peoples R China
[2] Jiaxing Univ, Coll Biol Chem Sci & Engn, 118 Jiahang Rd, Jiaxing 314001, Peoples R China
[3] Nanjing Forestry Univ, Coll Sci, Nanjing 210037, Peoples R China
基金
中国国家自然科学基金;
关键词
cross-electrophile coupling; nickel; aryl phosphate; magnesium; lithium chloride; biaryl; NEGISHI COUPLINGS; DIRECT INSERTION; ALKYL-HALIDES; REAGENTS; ALKENYL; LIGAND; REACTIVITY; ACCESS;
D O I
10.1002/adsc.202300663
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A step-economical and operationally simple nickel-catalyzed cross-electrophile coupling of aryl phosphates with aryl bromides through C-O bond cleavage, which precluded the employment of relatively moisture-labile and unreadily available organometallics, was developed. The reaction proceeded smoothly in the presence of magnesium turnings and lithium chloride in THF to afford the corresponding biaryls in moderate to good yields with reasonable functionality tolerance.
引用
收藏
页码:2511 / 2515
页数:5
相关论文
共 50 条
  • [31] Synthesis of (Hetero)biaryls via Nickel Catalyzed Reductive Cross-Electrophile Coupling Between (Hetero)aryl Iodides and Bromides
    Surgenor, Richard R.
    Lee, Hyelee
    CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (44)
  • [32] Amine-Borane-Mediated, Nickel/Photoredox-Catalyzed Cross-Electrophile Coupling between Alkyl and Aryl Bromides
    Li, Ke-Rong
    He, Xian-Chen
    Gao, Jie
    Liu, Yan-Ling
    Chen, Hong-Bin
    Xiang, Hao-Yue
    Chen, Kai
    Yang, Hua
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (17): : 12658 - 12667
  • [33] Nickel-Catalyzed Cross-Electrophile 1,2-Silyl-Arylation of 1,3-Dienes with Chlorosilanes and Aryl Bromides
    Pan, Qiu-Quan
    Qi, Liangliang
    Pang, Xiaobo
    Shu, Xing-Zhong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (04)
  • [34] Nickel-Catalyzed Cross-Coupling of Aryl Phosphates with Arylboronic Acids
    Chen, Hu
    Huang, Zhongbin
    Hu, Xiaoming
    Tang, Guo
    Xu, Pengxiang
    Zhao, Yufen
    Cheng, Chien-Hong
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (07): : 2338 - 2344
  • [35] Nickel-catalyzed cross-electrophile coupling reactions of vinyl halides
    Johnson, Keywan
    Weix, Daniel
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
  • [36] Nickel-catalyzed cross-electrophile coupling reactions of diol derivatives
    Sanford, Amberly
    Thane, Taylor
    Jarvo, Elizabeth
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
  • [37] Nickel-Catalyzed Cross-Electrophile Coupling Reactions of Alcohols and Their Derivatives
    Jana, Sayan K.
    Maji, Biplab
    SYNTHESIS-STUTTGART, 2025,
  • [38] Nickel-catalyzed stereospecific cross-coupling and cross-electrophile coupling reactions
    Jarvo, Elizabeth
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 258
  • [39] Nickel-Catalyzed Asymmetric Cross-Electrophile trans-Aryl- Benzylation of α-Naphthyl Propargylic Alcohols
    Lin, Zhiyang
    Hu, Weitao
    Zhang, Linchuan
    Wang, Chuan
    ACS CATALYSIS, 2023, 13 (10) : 6795 - 6803
  • [40] Nickel-catalyzed stereospecific reductive cross-electrophile coupling reactions
    Jarvo, Elizabeth
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254