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
  • [41] Photoredox Catalysis Unlocks the Nickel-Catalyzed Cyanation of Aryl Halides under Benign Conditions
    Jia, Yue
    Liu, Yi-Yin
    Lu, Liang-Qiu
    Liu, Shi-Han
    Zhou, Hong-Bin
    Lan, Yu
    Xiao, Wen-Jing
    CCS CHEMISTRY, 2022, 4 (05): : 1577 - 1586
  • [42] Copper(II) acetate-catalysed conversion of aldoximes to amides under mild conditions
    Ma, Xiaoyun
    Lu, Ming
    JOURNAL OF CHEMICAL RESEARCH, 2016, (10) : 594 - 596
  • [43] Heterogeneous palladium-catalysed Heck reaction of aryl chlorides and styrene in water under mild conditions
    Mukhopadhyay, S
    Rothenberg, G
    Joshi, A
    Baidossi, M
    Sasson, Y
    ADVANCED SYNTHESIS & CATALYSIS, 2002, 344 (3-4) : 348 - 354
  • [44] Polymer supported Pd catalyzed thioester synthesis via carbonylation of aryl halides under phosphine free conditions
    Islam, Sk Manirul
    Molla, Rostam Ali
    Roy, Anupam Singha
    Ghosh, Kajari
    RSC ADVANCES, 2014, 4 (50) : 26181 - 26192
  • [45] Amide synthesis via nickel-catalysed reductive aminocarbonylation of aryl halides with nitroarenes
    Cheung, Chi Wai
    Ploeger, Marten Leendert
    Hu, Xile
    CHEMICAL SCIENCE, 2018, 9 (03) : 655 - 659
  • [46] HYDRODEHALOGENATION OF POLYCHLORINATED AROMATIC HALIDES BY HYPOPHOSPHITE WITH PD/C CATALYST UNDER MULTIPHASE CONDITIONS
    MARQUES, CA
    SELVA, M
    TUNDO, P
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (04): : 529 - 533
  • [47] Isolation of the reactive intermediate in palladium-catalysed coupling of secondary phosphine-boranes with aryl halides
    Gaumont, AC
    Hursthouse, MB
    Coles, SJ
    Brown, JM
    CHEMICAL COMMUNICATIONS, 1999, (01) : 63 - 64
  • [48] A terphenyl phosphine as a highly efficient ligand for palladium-catalysed amination of aryl halides with 1° anilines
    Zhou, Fabin
    Zhang, Lixue
    Shi, Ji-cheng
    JOURNAL OF CATALYSIS, 2021, 402 : 238 - 243
  • [49] A terphenyl phosphine as a highly efficient ligand for palladium-catalysed amination of aryl halides with 1° anilines
    Zhou, Fabin
    Zhang, Lixue
    Shi, Ji-cheng
    Journal of Catalysis, 2021, 402 : 238 - 243
  • [50] Complete Hydrodehalogenation of Polyfluorinated and Other Polyhalogenated Benzenes under Mild Catalytic Conditions
    Baumgartner, Rebekka
    Stieger, Greta K.
    McNeill, Kristopher
    ENVIRONMENTAL SCIENCE & TECHNOLOGY, 2013, 47 (12) : 6545 - 6553