Nickel-Catalyzed Negishi Cross-Coupling of Bromodifluoroacetamides

被引:44
|
作者
Tarui, Atsushi [1 ]
Shinohara, Saori [1 ]
Sato, Kazuyuki [1 ]
Omote, Masaaki [1 ]
Ando, Akira [1 ]
机构
[1] Setsunan Univ, Fac Pharmaceut Sci, 45-1 Nagaotogecho, Hirakata, Osaka 5730101, Japan
关键词
ARYL BORONIC ACIDS; FORMING REDUCTIVE ELIMINATION; FLUORO-BETA-LACTAM; ETHYL BROMODIFLUOROACETATE; MEDICINAL CHEMISTRY; ARYLBORONIC ACIDS; ALPHA-ARYLATION; COPPER; ARENES; PD;
D O I
10.1021/acs.orglett.6b00232
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A nickel-catalyzed Negishi coupling of bromodifluoroacetamides with arylzinc reagents has been developed. This reaction allows access to difluoromethylated aromatic compounds containing a variety of aryl groups and amide moieties. Furthermore, highly effective transformation of the functionalized difluoromethyl group (-(CF2CONRR2)-R-1) was realized via microwave-assisted reduction under mild conditions. The notable features of this strategy are its generality and its use of a low-cost nickel catalyst and ligand; thus, this reaction provides a facile method for applications in drug discovery and development.
引用
收藏
页码:1128 / 1131
页数:4
相关论文
共 50 条
  • [31] Nickel-Catalyzed Cross-Coupling of Aryltrimethylammonium Iodides with Organozinc Reagents
    Xie, Lan-Gui
    Wang, Zhong-Xia
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (21) : 4901 - 4904
  • [32] NICKEL-CATALYZED CROSS-COUPLING REACTION OF ALLYL HALIDES WITH ALKYNYLTINS
    CUI, DM
    HASHIMOTO, N
    IKEDA, S
    SATO, Y
    JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (18): : 5752 - 5756
  • [33] Nickel-catalyzed oxidative cross-coupling of arylboronic acids with olefins
    Liu, Dong
    Liu, Chao
    Lei, Aiwen
    PURE AND APPLIED CHEMISTRY, 2014, 86 (03) : 321 - 328
  • [34] 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
  • [35] Nickel-Catalyzed Cross-Coupling of Chromene Acetals and Boronic Acids
    Graham, Thomas J. A.
    Doyle, Abigail G.
    ORGANIC LETTERS, 2012, 14 (06) : 1616 - 1619
  • [36] 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
  • [37] Synthetic Applications of Nickel-Catalyzed Cross-Coupling and Cyclisation Reactions
    Durandetti, Muriel
    CHEMICAL RECORD, 2021, 21 (12): : 3746 - 3757
  • [38] Nickel-Catalyzed Reductive Cross-Coupling of Unactivated Alkyl Halides
    Yu, Xiaolong
    Yang, Tao
    Wang, Shulin
    Xu, Hailiang
    Gong, Hegui
    ORGANIC LETTERS, 2011, 13 (08) : 2138 - 2141
  • [39] Stereospecific nickel-catalyzed cross-coupling reactions of benzylic ethers
    Taylor, Buck L. H.
    Harris, Michael R.
    Swift, Elizabeth C.
    Jarvo, Elizabeth R.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [40] Nickel-Catalyzed Cross-Coupling of Diarylborinic Acids with Aryl Chlorides
    Chen, Xiaofeng
    Ke, Haihua
    Zou, Gang
    ACS CATALYSIS, 2014, 4 (02): : 379 - 385