Aerobic oxidation of alkyl aromatics to ketones catalyzed by biomimetic copper complex and N-hydroxyphthalimide (NHPI) under mild conditions

被引：4
|
作者：
Huang, Jia-Ying [1 ]
Liu, Xiao-Hui [1 ]
Wen, Tian-Tian [1 ]
Zhou, Xian-Tai [1 ,2 ]
机构：
[1] Sun Yat Sen Univ, Sch Chem Engn & Technol, Zhuhai 519082, Peoples R China
[2] Sun Yat Sen Univ, Huizhou Res Inst, Huizhou 516081, Peoples R China
来源：
MOLECULAR CATALYSIS | 2024年 / 552卷
基金：
中国国家自然科学基金;
关键词：
Biomimetic catalysis; Galactose oxidase; Catalytic oxidation; Molecular oxygen; N-Hydroxyphthalimide; C-H BOND; CHLOROPERBENZOIC ACID; MOLECULAR-OXYGEN; HYDROCARBONS; ACTIVATION; ALCOHOLS; LIGAND; MODEL;
D O I：
10.1016/j.mcat.2023.113673
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 galactose oxidase-like copper complex (CuIIL) (Ligand: N, N '-bis(2-hydroxy-3,5-di-tert-butylphenyl)-2,2 '-dia- minobiphenyl) was synthesized and used to catalyze the aerobic oxidation of alkyl aromatics to ketones in presence of N-hydroxyphthalimide (NHPI). The catalytic system exhibited excellent performance and tolerance under mild conditions. Mechanistic studies indicated that NHPI could be activated smoothly to generate phthalimide N-oxyl (PINO) radical in the presence of CuIIL. The kinetic isotope effect (KIE) studies showed that the generation of PINO radical was the rate-determining step.
引用
收藏
页数：8
相关论文
共 50 条
  • [1] Cobalt/N-Hydroxyphthalimide(NHPI)-Catalyzed Aerobic Oxidation of Hydrocarbons with Ionic Liquid Additive
    Mahmood, Sajid
    Xu, Bao-Hua
    Ren, Tian-Lu
    Zhang, Zhi-Bo
    Liu, Xiao-Min
    Zhang, Suo-Jiang
    MOLECULAR CATALYSIS, 2018, 447 : 90 - 96
  • [2] Synthesis of naphthalenediols by aerobic oxidation of diisopropylnaphthalenes catalyzed by N-hydroxyphthalimide (NHPI)/α,α′-azobisisobutyronitrile (AIBN)
    Aoki, Y
    Sakaguchi, S
    Ishii, Y
    ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (2-3) : 199 - 202
  • [3] N-Hydroxyphthalimide Catalyzed Aerobic Oxidation of Aldehydes under Continuous Flow Conditions
    Nagy, Bence S.
    Kappe, C. Oliver
    otvos, Sandor B.
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (12) : 1998 - 2008
  • [4] Selective oxidation of ethylbenzene by a biomimetic combination:: Hemin and N-hydroxyphthalimide (NHPI)
    Ma, Hong
    Xu, Jie
    Zhang, Qiaohong
    Miao, Hong
    Wu, Wenhai
    CATALYSIS COMMUNICATIONS, 2007, 8 (01) : 27 - 30
  • [5] Selective aerobic radical epoxidation of α-olefins catalyzed by N-hydroxyphthalimide (NHPI)
    Punta, Carlo
    Moscatelli, Davide
    Porta, Ombretta
    Minisci, Francesco
    Recupero, Francesco
    Gambarotti, Cristian
    Lucarini, Marco
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234
  • [6] Aerobic oxidation of N-alkylamides catalyzed by N-hydroxyphthalimide under mild conditions.: Polar and enthalpic effects
    Minisci, F
    Punta, C
    Recupero, F
    Fontana, F
    Pedulli, GF
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (08): : 2671 - 2676
  • [7] Aerobic oxidation of alcohols using a novel combination of N-hydroxyphthalimide (NHPI) and CuBr
    Yang, Gang
    Wang, Lianyue
    Li, Jun
    Zhang, Yi
    Dong, Xiaoli
    Lv, Ying
    Gao, Shuang
    RESEARCH ON CHEMICAL INTERMEDIATES, 2012, 38 (3-5) : 775 - 783
  • [8] Aerobic oxidation of alcohols using a novel combination of N-hydroxyphthalimide (NHPI) and CuBr
    Gang Yang
    Lianyue Wang
    Jun Li
    Yi Zhang
    Xiaoli Dong
    Ying Lv
    Shuang Gao
    Research on Chemical Intermediates, 2012, 38 : 775 - 783
  • [9] An Efficient and Mild Oxidation of α-isophorone to Ketoisophorone Catalyzed by N-Hydroxyphthalimide and Copper Chloride
    Chen, Lihua
    Tang, Ruiren
    Li, Zhongying
    Liang, Shan
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2012, 33 (02): : 459 - 463
  • [10] Aerobic oxidation of hydrocarbons using N-hydroxyphthalimide (NHPI) catalysts for cetane enhancement
    Al-Taher, Maryam M.
    Kalamaras, Christos
    Alqahtani, Mohammed A.
    Alomar, Fatimah S.
    FUEL, 2022, 324
12345