Nickel-catalyzed N-arylation of amines with arylboronic acids under open air

被引:17
|
作者
Ando, Shin [1 ]
Hirota, Yurina [1 ]
Matsunaga, Hirofumi [1 ]
Ishizuka, Tadao [1 ]
机构
[1] Kumamoto Univ, Fac Life Sci, Chuo Ku, 5-1 Oe Honmachi, Kumamoto 8620973, Japan
关键词
NHC; Nickel catalyst; Chan-Lam; C-N coupling; DYNAMIC KINETIC RESOLUTION; HETEROATOM BOND FORMATION; CROSS-COUPLING REACTIONS; C-N; ARYL; COMPLEXES; ETHERS; LIGAND; ESTERS; TRANSMETALATION;
D O I
10.1016/j.tetlet.2019.04.004
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this study, a well-defined, novel NHC-Ni complex was developed and used to catalyze the N-arylation of alkyl- and arylamines with arylboronic acids in a rare version of Chan-Lam coupling. Although the same coupling using copper catalysts has been widely studied, the nickel-catalyzed version is rare and normally requires 10-20 mol% catalyst loading. This novel NHC-Ni complex in combination with 4,4'-dimethyl-2,2'-bipyridine, however, proved to be an effective catalyst that lowered the required catalyst loading to only 2.0 mol%. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1277 / 1280
页数:4
相关论文
共 50 条
  • [1] Nickel-Catalyzed N-Arylation of Fluoroalkylamines
    McGuire, Ryan T.
    Yadav, Arun A.
    Stradiotto, Mark
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (08) : 4080 - 4084
  • [2] Nickel-Catalyzed N-Arylation of C-Amino-1,2,4-triazoles with Arylboronic Acids
    A. Yu. Chernenko
    V. A. Baydikova
    A. V. Astakhov
    M. E. Minyaev
    V. M. Chernyshev
    Doklady Chemistry, 2022, 504 : 93 - 99
  • [3] Nickel-Catalyzed N-Arylation of C-Amino-1,2,4-triazoles with Arylboronic Acids
    Chernenko, A. Yu
    Baydikova, V. A.
    Astakhov, A., V
    Minyaev, M. E.
    Chernyshev, V. M.
    DOKLADY CHEMISTRY, 2022, 504 (02) : 93 - 99
  • [4] A simple copper salt catalyzed N-arylation of amines, amides, imides, and sulfonamides with arylboronic acids
    Lan, JB
    Zhang, GL
    Yu, XQ
    You, JS
    Chen, L
    Yan, M
    Xie, RG
    SYNLETT, 2004, (06) : 1095 - 1097
  • [5] Nickel-catalyzed N-arylation of benzophenone hydrazone with bromoarenes
    Wu, Wei
    Fan, Xin-Heng
    Zhang, Li-Peng
    Yang, Lian-Ming
    RSC ADVANCES, 2014, 4 (07): : 3364 - 3367
  • [6] Nickel-Catalyzed N-Arylation of Diarylamines for Triarylamine Synthesis
    Hu, Kunjun
    Gao, Yunlong
    Jin, Jian
    ORGANOMETALLICS, 2022, 41 (05) : 509 - 513
  • [7] Copper-Catalyzed N-Arylation of Sulfoximines with Arylboronic Acids under Mild Conditions
    Gupta, Surabhi
    Baranwal, Siddharth
    Muniyappan, Nalluchamy
    Sabiah, Shahulhameed
    Kandasamy, Jeyakumar
    SYNTHESIS-STUTTGART, 2019, 51 (10): : 2171 - 2182
  • [8] Open-air N-arylation of N–H heterocycles with arylboronic acids catalyzed by copper(II) Schiff base complexes
    S. M. Islam
    Ram Chandra Dey
    Anupam Singha Roy
    Sumantra Paul
    Sanchita Mondal
    Transition Metal Chemistry, 2014, 39 : 961 - 969
  • [9] Solvent-free N-arylation of amines with arylboronic acids under ball milling conditions
    Zhu, Xingyi
    Zhang, Qihong
    Su, Weike
    RSC ADVANCES, 2014, 4 (43): : 22775 - 22778
  • [10] Rhodium-Catalyzed N-Arylation Addition of Arylboronic Acids to Ketimines
    Qian, Xue-Wei
    Sun, Xing-Wen
    CHINESE JOURNAL OF CHEMISTRY, 2024, 42 (18) : 2243 - 2248