Nickel-Catalyzed Direct Cross-Coupling of Unactivated Aryl Fluorides with Aryl Bromides

被引:12
|
作者
Ren, Jing-Ao [1 ]
Na, Jin-He [1 ]
Gui, Chao [1 ]
Miao, Chengping [2 ]
Chu, Xue-Qiang [1 ]
Ma, Mengtao [3 ]
Xu, Hao [1 ]
Zhou, Xiaocong [1 ,2 ]
Shen, Zhi-Liang [1 ]
机构
[1] Nanjing Tech Univ, Tech Inst Fluorochemistry 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
POLYFLUOROALKYL KETONES; HALIDES; ACTIVATION;
D O I
10.1021/acs.orglett.3c02000
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A nickel-catalyzeddirect cross-coupling of unactivated aryl fluorideswith aryl bromides is realized. The one-pot reaction, which avoidsthe use of preformed and sensitive organometallic reagents, proceedseffectively via C-F bond cleavage at room temperature in THFin the presence of the phosphine ligand and magnesium powder (withor without TMSCl) to produce the desired biaryls in modest to goodyields.
引用
收藏
页码:5525 / 5529
页数:5
相关论文
共 50 条
  • [1] Nickel-Catalyzed Direct Cross-Coupling of Aryl Fluorosulfates with Aryl Bromides
    Na, Jin-He
    Liu, Xiang
    Jing, Jia-Wen
    Wang, Jing
    Chu, Xue-Qiang
    Ma, Mengtao
    Xu, Hao
    Zhou, Xiaocong
    Shen, Zhi-Liang
    [J]. ORGANIC LETTERS, 2023, 25 (13) : 2318 - 2322
  • [2] Nickel-Catalyzed Cross-Coupling of Aryl Diazonium Salts with Aryl Bromides
    Zhang, Guofu
    Fu, Yu
    Xiang, Jicong
    Guan, Chenfei
    Sang, Zhimin
    Ding, Chengrong
    [J]. ORGANIC LETTERS, 2024, 26 (31) : 6687 - 6691
  • [3] Nickel-Catalyzed Desulfonylative Reductive Cross-Coupling of Aryl Sulfones with Aryl Bromides
    Huang, Xinmiao
    Tang, Ling
    Song, Zhiyong
    Jiang, Shuangshuang
    Liu, Xianmao
    Ma, Ming
    Chen, Bo
    Ma, Yuanhong
    [J]. ORGANIC LETTERS, 2023, : 1198 - 1203
  • [4] Nickel-Catalyzed Cross-Coupling Reaction of Aryl Methyl Sulfides with Aryl Bromides
    Zhong, Chuntao
    Liu, Mengna
    Qiu, Xianchao
    Wei, Hao
    Cui, Benqiang
    Shi, Yanhui
    Cao, Changsheng
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (19): : 13418 - 13426
  • [5] Nickel-catalyzed direct cross-coupling of heterocyclic phosphonium salts with aryl bromides
    Cui, Yan-Ying
    Li, Wen-Xin
    Ma, Na-Na
    Shen, Chuanji
    Zhou, Xiaocong
    Chu, Xue-Qiang
    Rao, Weidong
    Shen, Zhi-Liang
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (24): : 6931 - 6936
  • [6] Nickel-Catalyzed Cross-Coupling of Ethyl Chlorofluoroacetate with Aryl Bromides
    Li, Han
    Sheng, Jie
    Wu, Bing-Bing
    Li, Yan
    Wang, Xi-Sheng
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2021, 16 (13) : 1741 - 1744
  • [7] Nickel-Catalyzed Cross-Coupling of Aryl Fluorides and Organozinc Reagents
    Zhu, Feng
    Wang, Zhong-Xia
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (10): : 4285 - 4292
  • [8] Nickel-Catalyzed Direct Cross-Coupling of Aryl Thioether with Aryl Bromide
    Ma, Na-Na
    Hu, Xuan-Bo
    Wu, Yuan-Shuai
    Zheng, Ya-Wen
    Ma, Mengtao
    Chu, Xue-Qiang
    Xu, Hao
    Luo, Haiqing
    Shen, Zhi-Liang
    [J]. ORGANIC LETTERS, 2023, 25 (10) : 1771 - 1775
  • [9] Nickel-Catalyzed Direct Cross-Coupling of Aryl Sulfonium Salt with Aryl Bromide
    Ma, Na-Na
    Ren, Jing-Ao
    Liu, Xiang
    Chu, Xue-Qiang
    Rao, Weidong
    Shen, Zhi-Liang
    [J]. ORGANIC LETTERS, 2022, 24 (10) : 1953 - 1957
  • [10] Photochemical Nickel-Catalyzed Reductive Migratory Cross-Coupling of Alkyl Bromides with Aryl Bromides
    Peng, Long
    Li, Zheqi
    Yin, Guoyin
    [J]. ORGANIC LETTERS, 2018, 20 (07) : 1880 - 1883