Recent progress in catalytic oxygenation of aromatic C-H groups with the environmentally benign oxidants H2O2and O2

被引:28
作者
Ottenbacher, Roman V. [1 ,2 ]
Talsi, Evgenii P. [1 ,2 ]
Bryliakov, Konstantin P. [1 ,2 ]
机构
[1] Novosibirsk State Univ, Fac Nat Sci, Pirogova 1, Novosibisk 630090, Russia
[2] Boreskov Inst Catalysis, Pr Lavrentieva 5, Novosibisk 630090, Russia
基金
俄罗斯基础研究基金会;
关键词
aromatic oxidation; C-H activation; electrophilic substitution; hydrogen peroxide; oxygen; vitamin K-3; ONE-POT SYNTHESIS; HYDROGEN-PEROXIDE; DIRECT HYDROXYLATION; SELECTIVE OXIDATION; BENZENE HYDROXYLATION; P-BENZOQUINONES; HETEROGENEOUS CATALYST; PHASE HYDROXYLATION; EFFICIENT OXIDATION; AEROBIC OXIDATION;
D O I
10.1002/aoc.5900
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Developing efficient approaches for the selective oxygenation of aromatic C-H groups has been a challenging goal, interesting from both fundamental and practical perspectives. Designing catalyst systems for the direct production of phenol from benzene holds significant practical promise; on the contrary, novel strategies for the late-stage selective introduction of oxygen into aromatic rings of complex organic molecules could be useful for the synthesis of fine chemicals, including biologically active compounds. Another aspect of the overall picture is toughening environmental constraints, resulting in a steady increase in the number of catalyst systems relying on environmentally benign oxidants such as H(2)O(2)and O-2. Overall, today, the realm of selective catalytic aromatic C-H oxidations is developing rapidly. This review summarizes the progress made in homo- and heterogeneous catalyst systems of aromatic C-H oxygenations with hydrogen peroxide and molecular oxygen, achieved in the last decade.
引用
收藏
页数:25
相关论文
共 133 条
[1]   Synergistic Effect between Ultrasmall Cu(II) Oxide and CuCr2O4 Spinel Nanoparticles in Selective Hydroxylation of Benzene to Phenol with Air as Oxidant [J].
Acharyya, Shankha Shubhra ;
Ghosh, Shilpi ;
Tiwari, Ritesh ;
Pendem, Chandrashekar ;
Sasaki, Takehiko ;
Bal, Rajaram .
ACS CATALYSIS, 2015, 5 (05) :2850-2858
[2]   Eclectic Hydroxylation of Benzene to Phenol Using Ferrites of Fe and Zn as Durable and Magnetically Retrievable Catalysts [J].
Al-Sabagh, A. M. ;
Yehia, F. Z. ;
Eshaq, Gh. ;
ElMetwally, A. E. .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2017, 5 (06) :4811-4819
[3]   Transition-Metal-Catalyzed Synthesis of Hydroxylated Arenes [J].
Alonso, Diego A. ;
Najera, Carmen ;
Pastor, Isidro M. ;
Yus, Miguel .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (18) :5274-5284
[4]   Single-step benzene hydroxylation by cobalt(ii) catalysts via a cobalt(iii)-hydroperoxo intermediate [J].
Anandababu, Karunanithi ;
Muthuramalingam, Sethuraman ;
Velusamy, Marappan ;
Mayilmurugan, Ramasamy .
CATALYSIS SCIENCE & TECHNOLOGY, 2020, 10 (08) :2540-2548
[5]  
[Anonymous], 2011, ANGEW CHEM, DOI DOI 10.1021/jacs.5b05903
[6]   Selective hydroxylation of benzene derivatives and alkanes with hydrogen peroxide catalysed by a manganese complex incorporated into mesoporous silica-alumina [J].
Aratani, Yusuke ;
Yamada, Yusuke ;
Fukuzumi, Shunichi .
CHEMICAL COMMUNICATIONS, 2015, 51 (22) :4662-4665
[7]   Liquid phase hydroxylation of benzene to phenol over vanadyl acetylacetonate supported on amine functionalized SBA-15 [J].
Bao, Yaohui ;
Jiang, Hong ;
Xing, Weihong ;
Chen, Rizhi ;
Fan, Yiqun .
REACTION KINETICS MECHANISMS AND CATALYSIS, 2015, 116 (02) :535-547
[8]   Cage-like Copper(II) Silsesquioxanes: Transmetalation Reactions and Structural, Quantum Chemical, and Catalytic Studies [J].
Bilyachenko, Alexey N. ;
Dronova, Marina S. ;
Yalymov, Alexey I. ;
Lamaty, Frederic ;
Bantreil, Xavier ;
Martinez, Jean ;
Bizet, Christelle ;
Shul'pina, Lidia S. ;
Korlyukov, Alexander A. ;
Arkhipov, Dmitry E. ;
Levitsky, Mikhail M. ;
Shubina, Elena S. ;
Kirillov, Alexander M. ;
Shul'pin, Georgiy B. .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (24) :8758-8770
[9]   Binuclear Cage-Like Copper(II) Silsesquioxane ("Cooling Tower") - Its High Catalytic Activity in the Oxidation of Benzene and Alcohols [J].
Bilyachenko, Alexey N. ;
Dronova, Marina S. ;
Yalymov, Alexey I. ;
Korlyukov, Alexander A. ;
Shul'pina, Lidia S. ;
Arkhipov, Dmitry E. ;
Shubina, Elena S. ;
Levitsky, Mikhail M. ;
Kirilin, Alexey D. ;
Shul'pin, Georgiy B. .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2013, 2013 (30) :5240-5246
[10]   Genotoxicity of streptonigrin:: a review [J].
Bolzán, AD ;
Bianchi, MS .
MUTATION RESEARCH-REVIEWS IN MUTATION RESEARCH, 2001, 488 (01) :25-37