Transition Metal-Catalyzed C-H Oxidation of Saturated Hydrocarbons with Molecular Oxygen

被引：9
|
作者：
Komiya, Naruyoshi [1 ,2 ]
Murahashi, Shun-Ichi [1 ]
机构：
[1] Osaka Univ, Grad Sch Engn Sci, Dept Chem, Toyonaka, Osaka 5608531, Japan
[2] Jikei Univ, Sch Med, Chem Lab, Chofu, Tokyo 1828570, Japan
来源：
CHEMICAL RECORD | 2021年 / 21卷 / 08期
基金：
日本学术振兴会;
关键词：
C-H oxidation; Saturated hydrocarbons; Molecular oxygen; Transition metal catalysts; CYTOCHROME-P-450 TYPE OXIDATION; BAEYER-VILLIGER OXIDATION; AEROBIC OXIDATION; ACYL CYANIDES; ENANTIOSELECTIVE OXIDATION; NICKEL(II) COMPLEXES; PERACETIC-ACID; SILYL ETHERS; RUTHENIUM; ALKANES;
D O I：
10.1002/tcr.202100154
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The C-H oxidation of saturated hydrocarbons to the corresponding alcohols and ketones can be performed efficiently at room temperature with molecular oxygen (1 atm) in the presence of acetaldehyde and catalysts such as Fe, Cu(OH)(2), and CuCl2-18-crown-6 complex. Moreover, extremely high turnover numbers (>27,000) have been obtained for the C-H oxidation of saturated hydrocarbons with molecular oxygen (1 atm) using a combination of Cu(OAc)(2) and acetonitrile at 70 degrees C. Related oxidation reactions such as epoxidation, Baeyer-Villiger reaction, acetoxylation of beta-lactams with molecular oxygen and a suitable aldehyde at room temperature are described.
引用
收藏
页码：1928 / 1940
页数：13
相关论文
共 50 条
  • [31] Synthesis of aryne precursors via transition metal-catalyzed C-H silylation
    Devaraj, Karthik
    Sollert, Carina
    Gates, Paul
    Pilarski, Lukasz
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [32] Metal-catalyzed C-H activation/functionalization: The fundamentals
    Roudesly, Fares
    Oble, Julie
    Poli, Giovanni
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2017, 426 : 275 - 296
  • [33] Metal-catalyzed C-H functionalization involving isocyanides
    Song, Bingrui
    Xu, Bin
    CHEMICAL SOCIETY REVIEWS, 2017, 46 (04) : 1103 - 1123
  • [34] Metal-Catalyzed C-H Bond Oxidation in the Total Synthesis of Natural and Unnatural Products
    Santana, Victor C. S.
    Fernandes, Milena C., V
    Cappuccelli, Isadora
    Richieri, Ana Carolina G.
    de Lucca Jr, Emilio C.
    SYNTHESIS-STUTTGART, 2022, 54 (24): : 5337 - 5359
  • [35] Recent Advances in Homogeneous Metal-Catalyzed Aerobic C-H Oxidation of Benzylic Compounds
    Urgoitia, Garazi
    SanMartin, Raul
    Teresa Herrero, Maria
    Dominguez, Esther
    CATALYSTS, 2018, 8 (12):
  • [36] Metal-Catalyzed C-H Bond Oxidation in the Total Synthesis of Natural and Unnatural Products
    Santana, Victor C. S.
    Fernandes, Milena C. V.
    Cappuccelli, Isadora
    Richieri, Ana Carolina G.
    De Lucca Jr, Emilio C.
    Synthesis (Germany), 2022, 54 (24) : 5337 - 5359
  • [37] Transition Metal-Catalyzed Regio-selective Aromatic C-H Bond Oxidation for C-O Bond Formation
    Yang, Fanzhi
    Zhang, Han
    Liu, Xuri
    Wang, Bo
    Lutz, Ackermann
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (01) : 59 - 73
  • [38] The Use of Ammonia as an Ultimate Amino Source in the Transition Metal-Catalyzed C-H Amination
    Kim, Hyunwoo
    Chang, Sukbok
    ACCOUNTS OF CHEMICAL RESEARCH, 2017, 50 (03) : 482 - 486
  • [39] Transition Metal-Catalyzed Regiodivergent C-H Arylations of Aryl-Substituted Azoles
    Liu, Linhao
    Durai, Manisha
    Doucet, Henri
    ENGINEERING ANALYSIS WITH BOUNDARY ELEMENTS, 2022, 138
  • [40] Transition Metal-Catalyzed Regiodivergent C-H Arylations of Aryl-Substituted Azoles
    Liu, Linhao
    Durai, Manisha
    Doucet, Henri
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (12)
12345