Ultrasonic activation of N-arylation of amines with aryl halides catalysed by iron (III)

2021 ◽  
Vol 18 ◽  
Author(s):  
Khemais Said ◽  
Ridha Ben Salem
Keyword(s):  
Aromatic Amines ◽  
Low Cost ◽  
Phenylboronic Acid ◽  
Coupling Reaction ◽  
Catalyst System ◽  
Aryl Halides ◽  
Environmentally Benign ◽  
Ultrasonic Activation ◽  
External Magnet ◽  
Considerable Loss

: A practical and promising protocol was developed for N-arylations of various aromatic amines. This protocol was carried out through the coupling reaction between various aryl halides and phenylboronic acid using iron (III). The processes are efficiently promoted by the catalyst system involving the environmentally benign iron (III) and the state PPh3. The advantages of this method are its versatility, convenient operation, and low cost, along with the yields, which are remarkably improved under ultrasonic irradiation, and the high purity of the products obtained. The catalyst can be magnetically recycled via an external magnet and reused several times without considerable loss of its catalytic activity.

scholarly journals A tetranuclear CuII2DyIII2 coordination cluster as a Suzuki (C–C) coupling reaction promoter

2018 ◽  
Vol 47 (48) ◽  
pp. 17202-17205 ◽  
Author(s):  
Prashant Kumar ◽  
Kieran Griffiths ◽  
Christopher E. Anson ◽  
Annie K. Powell ◽  
George E. Kostakis
Keyword(s):  
Phenylboronic Acid ◽  
Coupling Reaction ◽  
Suzuki Coupling ◽  
Aryl Halides ◽  
Environmentally Benign ◽  
Suzuki Coupling Reaction

The air stable and high yielding tetranuclear coordination cluster [CuII2DyIII2L4(NO3)2(CH3CN)2]·2(CH3CN) promotes the Suzuki coupling reaction of phenylboronic acid with substituted aryl halides under environmentally benign conditions.

Fluorescence labeling method for aryl halides with 4-(4,5-diphenyl-1H-imidazol-2-yl)phenylboronic acid based on Suzuki coupling reaction

2005 ◽  
Vol 1066 (1-2) ◽  
pp. 119-125 ◽  
Author(s):  
Naotaka Kuroda ◽  
Sumika Sugihara ◽  
Yohko Sugihara ◽  
Mitsuhiro Wada ◽  
Naoya Kishikawa ◽  
...  
Keyword(s):  
Phenylboronic Acid ◽  
Coupling Reaction ◽  
Suzuki Coupling ◽  
Aryl Halides ◽  
Fluorescence Labeling ◽  
Suzuki Coupling Reaction ◽  
Labeling Method

ChemInform Abstract: CuS/Fe: A Novel and Highly Efficient Catalyst System for Coupling Reaction of Aryl Halides with Diaryl Diselenides.

ChemInform ◽  
2011 ◽  
Vol 42 (8) ◽  
pp. no-no
Author(s):  
Yaming Li ◽  
Huifeng Wang ◽  
Xiaoying Li ◽  
Tao Chen ◽  
Defeng Zhao
Keyword(s):  
Coupling Reaction ◽  
Catalyst System ◽  
Aryl Halides ◽  
Efficient Catalyst ◽  
Highly Efficient

scholarly journals Fluorogenic derivatization of aryl halides based on the formation of biphenyl by Suzuki coupling reaction with phenylboronic acid

2009 ◽  
Vol 1216 (40) ◽  
pp. 6873-6876 ◽  
Author(s):  
Naoya Kishikawa ◽  
Kimiko Kubo ◽  
Sherin Farouk Hammad ◽  
Mokhtar Mohamed Mabrouk ◽  
Ahmed Habib ◽  
...  
Keyword(s):  
Phenylboronic Acid ◽  
Coupling Reaction ◽  
Suzuki Coupling ◽  
Aryl Halides ◽  
Suzuki Coupling Reaction ◽  
Fluorogenic Derivatization

CuS/Fe: a novel and highly efficient catalyst system for coupling reaction of aryl halides with diaryl diselenides

Tetrahedron ◽  
2010 ◽  
Vol 66 (45) ◽  
pp. 8583-8586 ◽  
Author(s):  
Yaming Li ◽  
Huifeng Wang ◽  
Xiaoying Li ◽  
Tao Chen ◽  
Defeng Zhao
Keyword(s):  
Coupling Reaction ◽  
Catalyst System ◽  
Aryl Halides ◽  
Efficient Catalyst ◽  
Highly Efficient

Proline-functionalized chitosan–palladium(ii) complex, a novel nanocatalyst for C–C bond formation in water

RSC Advances ◽  
2015 ◽  
Vol 5 (31) ◽  
pp. 24742-24748 ◽  
Author(s):  
A. R. Hajipour ◽  
E. Boostani ◽  
F. Mohammadsaleh
Keyword(s):  
Phenylboronic Acid ◽  
Bond Formation ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Environmentally Friendly ◽  
Aryl Halides ◽  
Heterogeneous Nanocatalyst ◽  
Cross Coupling Reaction

An environmentally friendly palladium-based catalyst supported on proline-functionalized chitosan was successfully prepared and evaluated as a heterogeneous nanocatalyst in the Suzuki cross-coupling reaction of various aryl halides with phenylboronic acid.

scholarly journals Synthesis and characterization of new 3,3`-bipyrazole-4,4`-dicarboxylic acid derivatives and some of their palladium(II) complexes as pre-catalyst for Suzuki coupling reaction in water

2019 ◽  
Vol 10 (4) ◽  
pp. 367-375 ◽  
Author(s):  
Othman Abduallah Al-Fulaij ◽  
Abdel-Zaher Abdelaziz Elassar ◽  
Kamal Mohamed Dawood
Keyword(s):  
Dicarboxylic Acid ◽  
Phenylboronic Acid ◽  
Cycloaddition Reaction ◽  
Coupling Reaction ◽  
Catalyst System ◽  
Suzuki Coupling Reaction ◽  
X Ray Crystallography ◽  
Cross Coupling Reaction ◽  
Pd Complexes

The 1,3-dipolar cycloaddition reaction of bis-hydrazonyl chlorides with methyl propiolate afforded dimethyl 1,1¢-aryl-3,3`-bipyrazole-4,4`-dicarboxylates (5a,b). Heating the later compound 5a with a mixture of HCl/AcOH gave 3,3`-bipyrazole-5,5`-dicarboxylic acid derivative 6. Treatment of the hydrazonoyl chloride (1a) and 3,3`-bipyrazole-5,5`-dicarboxylic acid (6) with palladium(II) chloride gave the corresponding Pd-complexes 7 and 8, respectively. The catalytic activity of the prepared Pd-complexes was examined in the Suzuki cross-coupling reaction of phenylboronic acid with activated and deactivated aryl(hetaryl) bromides. The catalyst system provides very good to excellent yields, 85-94%. The structures of the obtained products were established from their elemental analysis, spectral data, XPS, EDX, and single crystal X-ray crystallography. Crystal data for C10H7N2O2 (6): triclinic, space group P-1 (no. 2), a = 3.9956(10) Å, b = 9.8917(18) Å, c = 10.810(3) Å, α = 94.167(15)°, β = 94.979(19)°, γ = 98.953(15)°, V = 418.83(16) Å3, Z = 2, T = 296.(2) K, μ(Cu Kα) = 0.887 mm-1, Dcalc = 1.484 g/cm3, 5469 reflections measured (11.72° ≤ 2Θ ≤ 133.24°), 1420 unique (Rint = 0.0633, Rsigma = 7.24%) which were used in all calculations. The final R1 was 0.1055 (>2sigma(I)) and wR2 was 0.3620 (all data).

Synthesis, Characterization and Catalytic Utilization of a Ferrocene Diamidodiphosphane

2007 ◽  
Vol 72 (4) ◽  
pp. 453-467 ◽  
Author(s):  
Petr Štěpnička ◽  
Jiří Schulz ◽  
Ivana Císařová ◽  
Karla Fejfarová
Keyword(s):  
Phenylboronic Acid ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Aryl Chlorides ◽  
Highly Active ◽  
Aryl Bromides ◽  
Cross Coupling Reaction

Amidation of 1'-(diphenylphosphanyl)ferrocene-1-carboxylic acid (Hdpf) with ethane-1,2-diamine afforded N,N'-ethylenebis[1'-(diphenylphosphanyl)ferrocene-1-carboxamide] (1), which was isolated in free and solvated form, 1·2AcOH. Both 1 and Hdpf were further converted to their respective phosphane sulfides, 2·2AcOH and 3 that were structurally characterized. Testing of the amidophosphane ligands in Suzuki-Miyaura cross-coupling reaction between phenylboronic acid and various aryl halides revealed that catalyst formed in situ from 1 and palladium(II) acetate is highly active in coupling reactions of aryl bromides whilst the corresponding aryl chlorides showed no or only poor conversions. The catalyst based on 2·2AcOH gave markedly lower yields of the coupling products.

Chiral Mn(III) Salen Complex Immobilized on CuFe2O4@SiO2-NH2 NPs: A Cheap and Efficient Catalyst for N-arylation of Aryl Halides and Phenylboronic Acid Under Mild Conditions

2020 ◽  
Vol 17 (11) ◽  
pp. 857-863
Author(s):  
Mohammad Ali Nasseri ◽  
Seyyedeh Ameneh Alavi ◽  
Milad Kazemnejadi ◽  
Ali Allahresani
Keyword(s):  
Phenylboronic Acid ◽  
Significant Loss ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Efficient Catalyst ◽  
Aryl Chlorides ◽  
Mild Conditions ◽  
Cross Coupling Reactions ◽  
Salen Complex ◽  
Ft Ir

A convenient and efficient chiral CuFe2O4@SiO2-Mn(III) Ch.salen nanocatalyst has been developed for the C-N cross-coupling reactions of aryl halides/ phenylboronic acid with N-heterocyclic compounds in water and/or DMSO under mild conditions. The catalyst could be applied for the N-arylation of a variety of nitrogen-containing heterocycles with aryl chlorides, bromides, iodides and phenylboronic acid under mild conditions. Moderate to good yields were achieved for all substrates. The structure of catalyst was characterized using various techniques including FT-IR, FE-SEM, EDX, XRD, TEM and TGA. The catalyst can be simply recovered and reused for several times without significant loss of activity.

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