Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 

Saved Queries

Sign in to use this feature.

Search Filter Reset All

Years

Between: -

Subjects

remove_circle_outline
remove_circle_outline
remove_circle_outline
Add Subjects Reset
Select Subjects

Journals

remove_circle_outline
remove_circle_outline
Add Journals Reset
Select Journals

Article Types

remove_circle_outline
remove_circle_outline
remove_circle_outline
Add Article Types Reset
Select Article Types

Countries / Regions

remove_circle_outline
remove_circle_outline
remove_circle_outline
remove_circle_outline
remove_circle_outline
remove_circle_outline
Add Countries / Regions Reset
Select Countries / Regions
Update Search
share announcement

Search Results (7)

Search Parameters:
Keywords = haloarenes

Order results
Result details
Results per page
Show export options expand_more Show export options expand_less
Select all
Export citation of selected articles as:
16 pages, 4949 KiB  
Article
Substitution Effects in Aryl Halides and Amides into the Reaction Mechanism of Ullmann-Type Coupling Reactions
by Rocío Durán, César Barrales-Martínez, Fabián Santana-Romo, Diego F. Rodríguez, Flavia C. Zacconi and Barbara Herrera
Molecules 2024, 29(8), 1770; https://doi.org/10.3390/molecules29081770 - 13 Apr 2024
Cited by 3 | Viewed by 2247
Abstract
In this article, we present a comprehensive computational investigation into the reaction mechanism of N-arylation of substituted aryl halides through Ullmann-type coupling reactions. Our computational findings, obtained through DFT ωB97X-D/6-311G(d,p) and ωB97X-D/LanL2DZ calculations, reveal a direct relation between the previously reported experimental [...] Read more.
In this article, we present a comprehensive computational investigation into the reaction mechanism of N-arylation of substituted aryl halides through Ullmann-type coupling reactions. Our computational findings, obtained through DFT ωB97X-D/6-311G(d,p) and ωB97X-D/LanL2DZ calculations, reveal a direct relation between the previously reported experimental reaction yields and the activation energy of haloarene activation, which constitutes the rate-limiting step in the overall coupling process. A detailed analysis of the reaction mechanism employing the Activation Strain Model indicates that the strain in the substituted iodoanilines is the primary contributor to the energy barrier, representing an average of 80% of the total strain energy. Additional analysis based on conceptual Density Functional Theory (DFT) suggests that the nucleophilicity of the nitrogen in the lactam is directly linked to the activation energies. These results provide valuable insights into the factors influencing energetic barriers and, consequently, reaction yields. These insights enable the rational modification of reactants to optimize the N-arylation process. Full article
►▼ Show Figures

Graphical abstract

11 pages, 763 KiB  
Article
Base-Promoted SNAr Reactions of Fluoro- and Chloroarenes as a Route to N-Aryl Indoles and Carbazoles
by Muhammad Asif Iqbal, Hina Mehmood, Jiaying Lv and Ruimao Hua
Molecules 2019, 24(6), 1145; https://doi.org/10.3390/molecules24061145 - 22 Mar 2019
Cited by 20 | Viewed by 8670
Abstract
KOH/DMSO-promoted C-N bond formation via nucleophilic aromatic substitution (SNAr) between chloroarenes or fluoroarenes with indoles and carbazole under transition metal-free conditions affording the corresponding N-arylated indoles and carbazoles has been developed. Full article
(This article belongs to the Special Issue Frontier in Green Chemistry Approaches II)
►▼ Show Figures

Graphical abstract

14 pages, 2790 KiB  
Article
Geometry Constrained N-(5,6,7-Trihydroquinolin-8-ylidene)arylaminopalladium Dichloride Complexes: Catalytic Behavior toward Methyl Acrylate (MA), Methyl Acrylate-co-Norbornene (MA-co-NB) Polymerization and Heck Coupling
by Yanning Zeng, Qaiser Mahmood, Tongling Liang and Wen-Hua Sun
Molecules 2016, 21(12), 1686; https://doi.org/10.3390/molecules21121686 - 7 Dec 2016
Cited by 13 | Viewed by 5853
Abstract
A new pair of plladium complexes (Pd4 and Pd5) ligated with constrained N-(5,6,7-trihydroquinolin-8-ylidene)arylamine ligands have been prepared and well characterized by 1H-, 13C-NMR and FTIR spectroscopies as well as elemental analysis. The molecular structure of Pd4 and Pd5 [...] Read more.
A new pair of plladium complexes (Pd4 and Pd5) ligated with constrained N-(5,6,7-trihydroquinolin-8-ylidene)arylamine ligands have been prepared and well characterized by 1H-, 13C-NMR and FTIR spectroscopies as well as elemental analysis. The molecular structure of Pd4 and Pd5 in solid state have also been determined by X-ray diffraction, showing slightly distorted square planar geometry around the palladium metal center. All complexes Pd1–Pd5 are revealed highly efficient catalyst in methyl acrylate (MA) polymerization as well as methyl acrylate/norbornene (MA/NB) copolymerization. In the case of MA polymerization, as high as 98.4% conversion with high molecular weight up to 6282 kg·mol−1 was achieved. Likewise, Pd3 complex has good capability to incorporate about 18% NB content into MA polymer chains. Furthermore, low catalyst loadings (0.002 mol %) of Pd4 or Pd5 are able to efficiently mediate the coupling of haloarenes with styrene affording up to 98% conversion. Full article
(This article belongs to the Special Issue Palladium Catalysts 2016)
►▼ Show Figures

Graphical abstract

20 pages, 853 KiB  
Communication
Electron Transfer-Induced Coupling of Haloarenes to Styrenes and 1,1-Diphenylethenes Triggered by Diketopiperazines and Potassium tert-Butoxide
by Eswararao Doni, Shengze Zhou and John A. Murphy
Molecules 2015, 20(2), 1755-1774; https://doi.org/10.3390/molecules20021755 - 22 Jan 2015
Cited by 30 | Viewed by 11155
Abstract
The coupling of haloarenes to styrenes and 1,1-diarylethenes has been achieved with potassium tert-butoxide in the presence of N,N'-dialkyldiketopiperazines. In contrast to previously reported reactions where phenanthroline has been used to mediate the reactions, the use of diketopiperazines can lead [...] Read more.
The coupling of haloarenes to styrenes and 1,1-diarylethenes has been achieved with potassium tert-butoxide in the presence of N,N'-dialkyldiketopiperazines. In contrast to previously reported reactions where phenanthroline has been used to mediate the reactions, the use of diketopiperazines can lead to either 1,1,2-triarylethenes or 1,1,2-triarylethanes, depending on the conditions used. Full article
(This article belongs to the Special Issue Free Radicals and Radical Ions)
►▼ Show Figures

Figure 1

8 pages, 99 KiB  
Article
Palladium on Carbon-Catalyzed Suzuki-Miyaura Coupling Reaction Using an Efficient and Continuous Flow System
by Tomohiro Hattori, Aya Tsubone, Yoshinari Sawama, Yasunari Monguchi and Hironao Sajiki
Catalysts 2015, 5(1), 18-25; https://doi.org/10.3390/catal5010018 - 12 Jan 2015
Cited by 45 | Viewed by 12113
Abstract
The continuous flow Suzuki-Miyaura reaction between various haloarenes and arylboronic acids was successfully achieved within only ca. 20 s during the single-pass through a cartridge filled with palladium on carbon (Pd/C). No palladium leaching was observed in the collected reaction solution by atomic [...] Read more.
The continuous flow Suzuki-Miyaura reaction between various haloarenes and arylboronic acids was successfully achieved within only ca. 20 s during the single-pass through a cartridge filled with palladium on carbon (Pd/C). No palladium leaching was observed in the collected reaction solution by atomic absorption spectrometry (detection limit: 1 ppm). Full article
(This article belongs to the Special Issue Palladium Catalysts for Cross-Coupling Reaction)
►▼ Show Figures

Graphical abstract

10 pages, 215 KiB  
Article
Cross-Coupling Reaction with Lithium Methyltriolborate
by Yasunori Yamamoto, Kazuya Ikizakura, Hajime Ito and Norio Miyaura
Molecules 2013, 18(1), 430-439; https://doi.org/10.3390/molecules18010430 - 28 Dec 2012
Cited by 12 | Viewed by 7171
Abstract
We newly developed lithium methyltriolborate as an air-stable white solid that is convenient to handle. The good performance of this triolborate for metal-catalyzed bond-forming reactions was demonstrated in palladium-catalyzed cross-coupling reactions with haloarenes. Cross-coupling reaction of [MeB(OCH2)3CCH3]Li [...] Read more.
We newly developed lithium methyltriolborate as an air-stable white solid that is convenient to handle. The good performance of this triolborate for metal-catalyzed bond-forming reactions was demonstrated in palladium-catalyzed cross-coupling reactions with haloarenes. Cross-coupling reaction of [MeB(OCH2)3CCH3]Li with aryl halides occurred in the presence of Pd(OAc)2/RuPhos complex in refluxing MeOH/H2O and the absence of bases. Full article
(This article belongs to the Special Issue Suzuki Reaction)
►▼ Show Figures

Scheme 1

12 pages, 65 KiB  
Review
Recent Advances in the Substitution Reactions of Triorganylstannyl Ions with Aromatic Compounds by the SRN1 Mechanism. Synthetic Applications
by Eduardo F. Córsico, Al Postigo and Roberto A. Rossi
Molecules 2000, 5(9), 1068-1079; https://doi.org/10.3390/50901068 - 11 Sep 2000
Cited by 3 | Viewed by 10627
Abstract
A review on the reactions of triorganyl stannyl ions with haloarenes is presented. Emphasis on the synthetic applications of the resulting triorganyl stannyl aryl compounds is made, with their inherent potential to build large molecules through the SRN1 sequence, i.e. ArX→ArSnR [...] Read more.
A review on the reactions of triorganyl stannyl ions with haloarenes is presented. Emphasis on the synthetic applications of the resulting triorganyl stannyl aryl compounds is made, with their inherent potential to build large molecules through the SRN1 sequence, i.e. ArX→ArSnR3→ArAr, which can be iteratively repeated when appropriately substituted substrates are chosen. Full article
►▼ Show Figures

Scheme 1

Show export options expand_more Show export options expand_less
Select all
Export citation of selected articles as:
 
Displaying article 1-50 on page 1 of 1.
Back to TopTop