Nickel-catalyzed cross-coupling of diphenylphosphine with vinyl bromides and chlorides as a route to diphenylvinylphosphines

被引：19
|
作者：
Shulyupin, MO [1 ]
Chirkov, EA [1 ]
Kazankova, MA [1 ]
Beletskaya, LP [1 ]
机构：
[1] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119992, Russia
来源：
SYNLETT | 2005年 / 04期
关键词：
cross-coupling; phosphorus; nickel; alkenylphosphines;
D O I：
10.1055/s-2005-863714
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient nickel-catalyzed reaction for the phosphination of vinyl bromides and chlorides was developed. The procedure uses a combination of up to 1 mol% of nickel acetylacetonate, triethylamine and dimethylformamide as a solvent. The double bond geometry of the vinyl halides was retained under the reaction conditions.
引用
收藏
页码：658 / 660
页数：3
相关论文
共 50 条
  • [1] Nickel-catalyzed C-P cross-coupling of diphenylphosphine oxide with aryl chlorides
    Zhang, Hong-Yu
    Sun, Meng
    Ma, Yan-Na
    Tian, Qiu-Ping
    Yang, Shang-Dong
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (48) : 9627 - 9633
  • [2] Nickel-Catalyzed Reductive Cross-Coupling of Vinyl Bromides with Unactivated Alkyl Halides
    Gu, Jun
    Qiu, Canbin
    Lu, Wenbin
    Qian, Qun
    Lin, Kunhua
    Gong, Hegui
    SYNTHESIS-STUTTGART, 2017, 49 (08): : 1867 - 1873
  • [3] Nickel-Catalyzed Enantioselective Cross-Coupling of N-Hydroxyphthalimide Esters with Vinyl Bromides
    Suzuki, Naoyuki
    Hofstra, Julie L.
    Poremba, Kelsey E.
    Reisman, Sarah E.
    ORGANIC LETTERS, 2017, 19 (08) : 2150 - 2153
  • [4] Nickel-catalyzed cross-coupling reactions of benzylic zinc reagents with aromatic bromides, chlorides and tosylates
    Schade, Matthias A.
    Metzger, Albrecht
    Hug, Stephan
    Knochel, Paul
    CHEMICAL COMMUNICATIONS, 2008, (26) : 3046 - 3048
  • [5] Nickel-Catalyzed Reductive Cross-Coupling of Heteroaryl Chlorides and Aryl Chlorides
    Mirabi, Bijan
    Marchese, Austin D.
    Lautens, Mark
    ACS CATALYSIS, 2021, 11 (20) : 12785 - 12793
  • [6] Nickel-Catalyzed Reductive Cross-Coupling of Alkyl Bromides and Chlorosilanes
    Xing, Mimi
    Cui, Huanhuan
    Zhang, Chun
    ORGANIC LETTERS, 2021, 23 (19) : 7645 - 7649
  • [7] Nickel-Catalyzed Cross-Coupling of Ethyl Chlorofluoroacetate with Aryl Bromides
    Li, Han
    Sheng, Jie
    Wu, Bing-Bing
    Li, Yan
    Wang, Xi-Sheng
    CHEMISTRY-AN ASIAN JOURNAL, 2021, 16 (13) : 1741 - 1744
  • [8] Nickel-Catalyzed Reductive Cross-Coupling of Oxalates Derived from α-Hydroxy Carbonyls with Vinyl Bromides
    Ye, Cheng
    Tong, Weiqi
    Wu, Fan
    SYNTHESIS-STUTTGART, 2022, 54 (09): : 2251 - 2257
  • [9] Nickel-Catalyzed Cross-Coupling of Sulfonamides With (Hetero)aryl Chlorides
    McGuire, Ryan T.
    Simon, Connor M.
    Yadav, Arun A.
    Ferguson, Michael J.
    Stradiotto, Mark
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (23) : 8952 - 8956
  • [10] Nickel-Catalyzed Reductive Cross-Coupling of Aziridines and Allylic Chlorides
    Liu, Shuai
    Wang, Sen-Lin
    Wan, Jie
    Peng, Shuang
    Zhang, Jie-Rui
    Ding, Hua-Jiao
    Zhang, Bin
    Ni, Hai-Liang
    Cao, Peng
    Hu, Ping
    Wang, Bi-Qin
    Chen, Bin
    ORGANIC LETTERS, 2023, 25 (35) : 6582 - 6586
12345