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
  • [31] Selective One-Step Aerobic Oxidation of Cyclohexane to E-Caprolactone Mediated by N-Hydroxyphthalimide (NHPI)
    Wang, Lingyao
    Zhang, Yuanbin
    Du, Renfeng
    Yuan, Haoran
    Wang, Yongtao
    Yao, Jia
    Li, Haoran
    CHEMCATCHEM, 2019, 11 (09) : 2260 - 2264
  • [32] Radical addition of ethers to alkenes under dioxygen catalyzed by N-hydroxyphthalimide (NHPI)/Co(OAC)2
    Hirano, K
    Sakaguchi, S
    Ishii, Y
    TETRAHEDRON LETTERS, 2002, 43 (20) : 3617 - 3620
  • [33] Synthesis of aromatic aldehydes by aerobic oxidation of hydroaromatic compounds and diarylalkanes using N-hydroxyphthalimide (NHPI) as a key catalyst
    Aoki, Y
    Sakaguchi, S
    Ishii, Y
    TETRAHEDRON, 2006, 62 (11) : 2497 - 2500
  • [34] Experimental and theoretical study on N-hydroxyphthalimide and its derivatives catalyzed aerobic oxidation of cyclohexylbenzene
    Yang, Yufei
    Ma, Jieyi
    Wu, Junyan
    Zhu, Weixia
    Zhang, Yadong
    CHINESE JOURNAL OF CHEMICAL ENGINEERING, 2022, 44 : 124 - 130
  • [35] Aerobic Oxidation of Methyl-substituted β-Carbolines Catalyzed by N-Hydroxyphthalimide and Metal Catalyst
    Qiu, Hongda
    Liang, Weida
    Zhang, Gongjun
    Lin, Miaoman
    Liu, Wanmin
    Gao, Zhanghua
    Wei, Wenting
    Tang, Chunlan
    Jin, Haixiao
    Liang, Hongze
    Yan, Xiaojun
    CHEMISTRYSELECT, 2018, 3 (43): : 12363 - 12366
  • [36] Aerobic oxidation of cycloalkenes catalyzed by iron metal organic framework containing N-hydroxyphthalimide
    Dhakshinamoorthy, Amarajothi
    Alvaro, Mercedes
    Garcia, Hermenegildo
    JOURNAL OF CATALYSIS, 2012, 289 : 259 - 265
  • [37] Experimental and theoretical study on N-hydroxyphthalimide and its derivatives catalyzed aerobic oxidation of cyclohexylbenzene
    Yufei Yang
    Jieyi Ma
    Junyan Wu
    Weixia Zhu
    Yadong Zhang
    ChineseJournalofChemicalEngineering, 2022, 44 (04) : 124 - 130
  • [38] Aerobic oxidation behavior of α-ionone catalyzed by N-hydroxyphthalimide combined with acetylacetone cobalt(II)
    Tang Rui-ren
    Zhou Ya-ping
    Gong Nian-hua
    Zhao Yu
    JOURNAL OF CENTRAL SOUTH UNIVERSITY OF TECHNOLOGY, 2008, 15 (04): : 474 - 478
  • [39] Aerobic oxidation behavior of α-ionone catalyzed by N-hydroxyphthalimide combined with acetylacetone cobalt(II)
    Rui-ren Tang
    Ya-ping Zhou
    Nian-hua Gong
    Yu Zhao
    Journal of Central South University of Technology, 2008, 15 : 474 - 478
  • [40] A new, highly selective, free-radical aerobic oxidation of silanes to silanols catalysed by N-hydroxyphthalimide under mild conditions.
    Minisci, F
    Recupero, F
    Punta, C
    Guidarini, C
    Fontana, F
    Pedulli, GF
    SYNLETT, 2002, (07) : 1173 - 1175
12345