Nickel-Catalyzed Decarboxylative Cross-Coupling of Perfluorobenzoates with Aryl Halides and Sulfonates

被引:38
|
作者
Sardzinski, Logan W. [1 ]
Wertjes, William C. [1 ]
Schnaith, Abigail M. [1 ]
Kalyani, Dipannita [1 ]
机构
[1] St Olaf Coll, Dept Chem, Northfield, MN 55057 USA
基金
美国国家卫生研究院;
关键词
CARBOXYLIC-ACIDS; POTASSIUM POLYFLUOROBENZOATES; ALLYL ARYL; ARYLATION; ETHERIFICATION; ALKENYLATION;
D O I
10.1021/acs.orglett.5b00241
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Ni-catalyzed method for the coupling of perfluorobenzoates with aryl halides and pseudohalides is described. Aryl iodides, bromides, chlorides, triflates, and tosylates participate in these transformations to afford the products in good yields. Penta-, tetra-, and trifluorinated biaryl compounds are obtained using these newly developed Ni-catalyzed decarboxylative cross-coupling reactions.
引用
收藏
页码:1256 / 1259
页数:4
相关论文
共 50 条
  • [1] Nickel-Catalyzed Reductive Cross-Coupling of Benzyl Halides with Aryl Halides
    Zhang, Qingchen
    Wang, Xuan
    Qian, Qun
    Gong, Hegui
    SYNTHESIS-STUTTGART, 2016, 48 (17): : 2829 - 2836
  • [2] Nickel-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylates with Aryl Tosylates and Mesylates
    Howard, Anna
    Klemann, Samantha
    Kolling, Sarah
    Little, Katrina
    Plasek, Erin
    Kalyani, Dipannita
    SYNTHESIS-STUTTGART, 2019, 51 (07): : 1603 - 1610
  • [3] Nickel-Catalyzed Paired Electrochemical Cross-Coupling of Aryl Halides with Nucleophiles
    Zhang, Yong
    Sun, Wenxuan
    Li, Chao
    SYNTHESIS-STUTTGART, 2022, 54 (02): : 281 - 294
  • [4] Nickel-Catalyzed Electrochemical Reductive Relay Cross-Coupling of Alkyl Halides to Aryl Halides
    Jiao, Ke-Jin
    Liu, Dong
    Ma, Hong-Xing
    Qiu, Hui
    Fang, Ping
    Mei, Tian-Sheng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (16) : 6520 - 6524
  • [5] Nickel-Catalyzed Reductive Decarboxylative Coupling of Diacyl Peroxides with Aryl/Vinyl Halides
    Qiu, Canbin
    Chen, Qifa
    Gong, Hegui
    ACS CATALYSIS, 2024, 14 (16): : 12192 - 12198
  • [6] Nickel-catalyzed Mizoroki-Heck cross-coupling reaction of aryl halides with styrenes
    Bhange, Dattatraya Soma
    Rasal, Nishant Kisan
    INDIAN JOURNAL OF CHEMISTRY, 2024, 63 (08): : 823 - 829
  • [7] 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
    ORGANIC LETTERS, 2022, 24 (10) : 1953 - 1957
  • [8] Preparation of Functionalized Aryl Iron(II) Compounds and a Nickel-Catalyzed Cross-Coupling with Alkyl Halides
    Wunderlich, Stefan H.
    Knochel, Paid
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (51) : 9717 - 9720
  • [9] Nickel-catalyzed decarboxylative cross-coupling of indole-3-acetic acids with aryl bromides by convergent paired electrolysis
    Wang, Zhen-Hua
    Wei, Lei
    Jiao, Ke-Jin
    Ma, Cong
    Mei, Tian-Sheng
    CHEMICAL COMMUNICATIONS, 2022, 58 (59) : 8202 - 8205
  • [10] Decarboxylative Cross-Coupling of Acyl Fluorides with Potassium Perfluorobenzoates
    Fu, Liyan
    Chen, Qiang
    Nishihara, Yasushi
    ORGANIC LETTERS, 2020, 22 (16) : 6388 - 6393