Organosulphur and organoselenium compounds as emerging building blocks for catalytic systems for O-arylation of phenols, a C-O coupling reaction

被引:24
|
作者
Sharma, Deepali [1 ]
Arora, Aayushi [1 ]
Oswal, Preeti [1 ]
Bahuguna, Anurag [1 ]
Datta, Anupama [2 ]
Kumar, Arun [1 ]
机构
[1] Doon Univ, Sch Phys Sci, Dept Chem, Dehra Dun 248012, Uttarakhand, India
[2] Inst Nucl Med & Allied Sci INMAS, Delhi, India
关键词
Aryl halides - Building blockes - Catalytic system - Coupling reaction - Diaryl ethers - Nano-catalyst - Organoselenium - Organoselenium compounds - Organosulfur - Organosulfur compounds;
D O I
10.1039/d1dt04371d
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Diaryl ethers form an important class of organic compounds. The classic copper-mediated Ullmann diaryl ether synthesis has been known for many years and involves the coupling of phenols with aryl halides. However, the use of high reaction temperature, high catalyst loading and expensive ligands has created a need for the development of alternative catalytic systems. In the recent past, organosulphur and organoselenium compounds have been used as building blocks for developing homogeneous, heterogeneous and nanocatalysts for this C-O coupling reaction. Homogeneous catalytic systems include preformed complexes of metals with organosulphur and organoselenium ligands. The performance of such complexes is influenced dramatically by the nature of the chalcogen (S or Se) donor site of the ligand. Nanocatalytic systems (including Pd17Se15, Pd16S7 and Cu1.8S) have been designed using a single-source precursor route. Heterogeneous catalytic systems contain either metal (Cu or Pd) or metal chalcogenides (Pd17Se15 or Cu1.8S) as catalytically active species. This article aims to cover the simple and straightforward methodologies and approaches that are adopted for developing catalytically relevant organosulfur and organoselenium ligands, their homogeneous metal complexes, heterogeneous and nanocatalysts. The effects of chalcogen (S or Se) donor, halogen (Cl/Br/I) of aryl halide, nature (electron withdrawing or electron donating) of substituents present on the aromatic ring of aryl halides or substituted phenols and position (ortho or para) of substitution on the results of catalytic reactions have been critically analyzed and summarized. The effect of composition (Pd17Se15 or Pd16S7) on the performance of nanocatalytic systems is also highlighted. Substrate scope has also been discussed in all three types of catalysis. The superiority of heterogeneous catalytic systems (e.g., Pd17Se15 immobilised on graphene oxide) indicates the bright future possibilities for the development of efficient catalytic systems using similar or tailored ligands for this reaction.
引用
收藏
页码:8103 / 8132
页数:30
相关论文
共 50 条
  • [31] DCID-mediated Heck cross-coupling of phenols via C-O bond activation
    Hosseini, Negin
    Mokhtari, Javad
    Yavari, Issa
    NEW JOURNAL OF CHEMISTRY, 2022, 46 (12) : 5588 - 5592
  • [32] Stable and reactive diacetyliminoxyl radical in oxidative C-O coupling with β-dicarbonyl compounds and their complexes
    Budnikov, Alexander S.
    Krylov, Igor B.
    Lastovko, Andrey, V
    Paveliev, Stanislav A.
    Romanenko, Alexander R.
    Nikishin, Gennady, I
    Terent'ev, Alexander O.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (35) : 7581 - 7586
  • [33] Magnetic CuFe2O4 Nanoparticles as an Efficient Catalyst for C-O Cross-Coupling of Phenols with Aryl Halides
    Zhang, Rongzhao
    Liu, Jianming
    Wang, Shoufeng
    Niu, Jianzhong
    Xia, Chungu
    Sun, Wei
    CHEMCATCHEM, 2011, 3 (01) : 146 - 149
  • [34] Ligand-Free Cu2O Nanowire Catalyzing C-N and C-O Coupling Reaction
    Dong, Qizhi
    Xiang, Jiannan
    Guo, Cancheng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2014, 34 (01) : 147 - 154
  • [35] Aryne reaction with trifluoromethyl ketones in three modes: C-C bond cleavage, [2+2] cycloaddition and O-arylation
    Yoshida, Hiroto
    Ito, Yu
    Yoshikawa, Yunito
    Ohshita, Joji
    Takaki, Ken
    CHEMICAL COMMUNICATIONS, 2011, 47 (30) : 8664 - 8666
  • [36] Bifunctional Photocatalysts Display Proximity-Enhanced Catalytic Activity in Metallaphotoredox C-O Coupling
    Dolcini, Luigi
    Solida, Andrea
    Lavelli, Daniele
    Hidalgo-Nunez, Andres Mauricio
    Gandini, Tommaso
    Fornara, Matthieu
    Colella, Alessandro
    Bossi, Alberto
    Penconi, Marta
    Fiorito, Daniele
    Gennari, Cesare
    Dal Corso, Alberto
    Pignataro, Luca
    ACS CATALYSIS, 2024, 14 (24): : 18651 - 18659
  • [37] Thermally stable and robust gadolinium-based metal-organic framework: Synthesis, structure and heterogeneous catalytic O-arylation reaction
    Ghosh, Pameli
    Maity, Tanmoy
    Biswas, Saptarshi
    Debnath, Rakesh
    Koner, Subratanath
    POLYHEDRON, 2021, 194
  • [38] Solvent-free palladium-catalyzed C-O cross-coupling of aryl bromides with phenols
    Rzhevskiy, Sergey A.
    Topchiy, Maxim A.
    Bogachev, Vasilii N.
    Minaeva, Lidiya, I
    Cherkashchenko, Ilia R.
    Lavrov, Konstantin, V
    Sterligov, Grigorii K.
    Nechaev, Mikhail S.
    Asachenko, Andrey F.
    MENDELEEV COMMUNICATIONS, 2021, 31 (03) : 409 - 411
  • [39] The first catalytic application of copper aluminate nanoparticles in C-C and C-O coupling reaction: green synthesis of some new αaEurolapachone derivatives
    Mori, Bahareh Abdolpour
    Khodabakhshi, Saeed
    Tajik, Sanaz
    Baghernejad, Mojtaba
    Yadegari, Amir
    MONATSHEFTE FUR CHEMIE, 2016, 147 (10): : 1849 - 1854
  • [40] Cellulose Oxidation and the Use of Carboxyl Cellulose Metal Complexes in Heterogeneous Catalytic Systems to Promote Suzuki-Miyaura Coupling and C-O Bond Formation Reaction
    Martins, Guilherme B. C.
    dos Santos, Marcelo R.
    Rodrigues, Marcus V. R.
    Sucupira, Renata R.
    Meneghetti, Luisa
    Monteiro, Adriano L.
    Suarez, Paulo A. Z.
    JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2017, 28 (11) : 2064 - 2072