Nickel(II) phosphine-catalysed hydrodehalogenation of aryl halides under mild ambient conditions

被引：3
|
作者：
Guek, Sebastian Jun Kai [1 ]
Ji, Li [2 ]
Loke, James Wen Liang [2 ]
Koh, Hwee Ling [1 ]
Fan, Wai Yip [2 ]
机构：
[1] Natl Univ Singapore, Dept Pharm, 18 Sci Dr 4, Singapore 117543, Singapore
[2] Natl Univ Singapore, Dept Chem, 3 Sci Dr 3, Singapore 117543, Singapore
来源：
MOLECULAR CATALYSIS | 2022年 / 524卷
关键词：
Hydrodehalogenation; Nickel phosphines; Aryl halides; Polyfluorinated arenes; Borohydride; POLYCHLORINATED-BIPHENYLS; COMPLEXES; HYDRODEFLUORINATION; REDUCTION;
D O I：
10.1016/j.mcat.2022.112310
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
A convenient and low-cost hydrodehalogenation process catalysed by air-stable nickel(II) complexes containing bidentate phosphine ligands has been developed under ambient conditions with sodium borohydride acting as the reducing agent and hydrogen atom source. High conversions of aryl halides, including polyfluorinated substrates, into their hydrogenated counterparts have been achieved in dimethylformamide (DMF) and to a moderate extent, in DMF/isopropanol (10:90% v/v) solvent mixture. A mechanism has been proposed to account for the experimental data.
引用
收藏
页数：8
相关论文
共 50 条
  • [1] Magnesium-promoted nickel-catalysed chlorination of aryl halides and triflates under mild conditions
    Zhang, Tian-Yu
    Bilal, Muhammad
    Wang, Tian-Zhang
    Zhang, Chao-Peng
    Liang, Yu-Feng
    CHEMICAL COMMUNICATIONS, 2024, 60 (84) : 12213 - 12216
  • [2] Phosphine-free Sonogashira coupling: reactions of aryl halides catalysed by palladium(II) complexes of azetidine-derived polyamines under mild conditions
    Lee, Dong-Hwan
    Lee, Young Hoon
    Harrowfield, Jack M.
    Lee, Ik-Mo
    Lee, Hong In
    Lim, Woo Taik
    Kim, Yang
    Jin, Myung-Jong
    TETRAHEDRON, 2009, 65 (08) : 1630 - 1634
  • [3] Nickel-catalyzed hydrodehalogenation of aryl halides
    Weidauer, Maik
    Irran, Elisabeth
    Someya, Chika I.
    Haberberger, Michael
    Enthaler, Stephan
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2013, 729 : 53 - 59
  • [4] Preparation of a cost-effective Ni-Ag bimetallic catalyst for hydrodehalogenation of aryl halides under mild conditions
    Deng, Jiazhu
    Xue, Teng
    Wu, Haihong
    Wu, Peng
    NEW JOURNAL OF CHEMISTRY, 2022, 46 (25) : 12169 - 12176
  • [5] Nickel(II)/Lewis acid catalysed olefin hydroamination and hydroarylation under mild conditions
    Li, Kaiwen
    Jiang, Hongwu
    Dong, Shuangfeng
    Li, Shuang-Long
    Chen, Zhuqi
    Yin, Guochuan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (04) : 823 - 830
  • [6] ORGN 692-The cyanation of aryl halides under mild conditions using bulky neopentyl phosphine ligands
    Hill, Lensey L.
    Shaughnessy, Kevin H.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2008, 235
  • [7] The conversion of phenols to the corresponding aryl halides under mild conditions
    Thompson, ALS
    Kabalka, GW
    Akula, MR
    Huffman, JW
    SYNTHESIS-STUTTGART, 2005, (04): : 547 - 550
  • [8] Pd-catalysed hydrodehalogenation of aryl chlorides: a mild method for deuteration and detoxification
    Burhenn, Angela
    Bavaro, Roberta
    Gessner, Viktoria H.
    CATALYSIS SCIENCE & TECHNOLOGY, 2023, 13 (12) : 3545 - 3550
  • [9] Rapid synthesis of aryl azides from aryl halides under mild conditions
    Andersen, J
    Madsen, U
    Björkling, F
    Liang, XF
    SYNLETT, 2005, (14) : 2209 - 2213
  • [10] Palladium-Catalyzed Hydroxylation of Aryl Halides under Ambient Conditions
    Sergeev, Alexey G.
    Schulz, Thomas
    Torborg, Christian
    Spannenberg, Anke
    Neumann, Helfried
    Beller, Matthias
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (41) : 7595 - 7599
12345