Nickel-Catalyzed Reductive Cross-Coupling of Benzyl Chlorides with Aryl Chlorides/Fluorides: A One-Pot Synthesis of Diarylmethanes

被引:52
|
作者
Zhang, Jie [1 ]
Lu, Gusheng [1 ]
Xu, Jin [1 ]
Sun, Hongmei [1 ]
Shen, Qj [1 ]
机构
[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
基金
中国国家自然科学基金;
关键词
IRON(III) AMINE-BIS(PHENOLATE) COMPLEXES; HETEROCYCLIC CARBENE LIGANDS; F BOND ACTIVATION; GRIGNARD-REAGENTS; ALKYL-HALIDES; ZINC REAGENTS; FUNCTIONALIZED DIARYLMETHANES; ARYLMAGNESIUM REAGENTS; ALLYLIC ACETATES; KETONE FORMATION;
D O I
10.1021/acs.orglett.6b01134
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first nickel-catalyzed, magnesium-mediated reductive cross-coupling between benzyl chlorides and aryl chlorides or fluorides is reported. A variety of diarylmethanes can be prepared in good to excellent yields in a one-pot manner using easy-to-access mixed PPh3/NHC Ni(II) complexes of Ni(PPh3)(NHC)Br-2 (NHC = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene, IPr, 1a; 1,3-di-tert-butylimidazol-2-ylidene, ItBu, 1b) as catalyst precursors. Activation of polychloroarenes or chemoselective cross-coupling based on the difference in catalytic activity between 1a and 1b is used to construct oligo-diarylmethane motifs.
引用
收藏
页码:2860 / 2863
页数:4
相关论文
共 50 条
  • [1] 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
  • [2] 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
  • [3] Nickel-catalyzed cross-coupling of aryl chlorides with aryl grignard reagents
    Bohm, Volker P. W.
    Weskamp, Thomas
    Gstottmayr, Christian W. K.
    Herrmann, Wolfgang A.
    1602, Wiley-VCH Verlag (39):
  • [4] Nickel-catalyzed cross-coupling of aryl chlorides with aryl Grignard reagents
    Böhm, VPW
    Weskamp, T
    Gstöttmayr, CWK
    Herrmann, WA
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, 39 (09) : 1602 - +
  • [5] 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
  • [6] Nickel-Catalyzed Cross-Coupling of Sulfonamides With (Hetero)aryl Chlorides
    McGuire, Ryan T.
    Simon, Connor M.
    Yadav, Arun A.
    Ferguson, Michael J.
    Stradiotto, Mark
    Advanced Materials, 2020, 59 (23) : 9037 - 9041
  • [7] Nickel-Catalyzed Cross-Coupling of Diarylborinic Acids with Aryl Chlorides
    Chen, Xiaofeng
    Ke, Haihua
    Zou, Gang
    ACS CATALYSIS, 2014, 4 (02): : 379 - 385
  • [8] P,N,N-Pincer nickel-catalyzed cross-coupling of aryl fluorides and chlorides
    Wu, Dan
    Wang, Zhong-Xia
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (33) : 6414 - 6424
  • [9] One-Pot Iron-Catalyzed Cross-Coupling Reactions of Aryl Chlorides and Aryl Bromides
    Yin, Yi-Bing
    Peng, Xiao-Shui
    Wong, Henry N. C.
    SYNTHESIS-STUTTGART, 2023, 55 (14): : 2253 - 2260
  • [10] Nickel-Catalyzed Cross-Coupling of (Hetero)aryl Chlorides with Aryllithium Compounds
    Tao, Jian-Long
    Wang, Zhong-Xia
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (04) : 521 - 527