scholarly journals Nucleophilic Aromatic Substitution of Polyfluoroarene to Access Highly Functionalized 10-Phenylphenothiazine Derivatives

2021 ◽  
Author(s):  
Kotaro Kikushima ◽  
Haruka Koyama ◽  
Kazuki Kodama ◽  
Toshifumi Dohi
Keyword(s):  
Aromatic Compounds ◽  
Nucleophilic Aromatic Substitution ◽  
Free Access ◽  
Aromatic Substitution ◽  
Halogen Bonds ◽  
Metal Free ◽  
Potential Applicability ◽  
Selective Substitution ◽  
Snar Reaction

Nucleophilic aromatic substitution (SNAr) reactions can provide metal-free access to synthesize mono-substituted aromatic compounds. We have developed efficient SNAr conditions for p-selective substitution of polyfluoroarenes with phenothiazine in the presence of a mild base to afford the corresponding 10-phenylphenothiazine (PTH) derivatives. The resulting polyfluoroarene-bearing PTH derivatives were subjected to a second SNAr reaction to generate highly functionalized PTH derivatives with potential applicability as photocatalysts for the reduction of carbon–halogen bonds.

scholarly journals Nucleophilic Aromatic Substitution of Polyfluoroarene to Access Highly Functionalized 10-Phenylphenothiazine Derivatives

Molecules ◽  
2021 ◽  
Vol 26 (5) ◽  
pp. 1365
Author(s):  
Kotaro Kikushima ◽  
Haruka Koyama ◽  
Kazuki Kodama ◽  
Toshifumi Dohi
Keyword(s):  
Aromatic Compounds ◽  
Nucleophilic Aromatic Substitution ◽  
Free Access ◽  
Aromatic Substitution ◽  
Halogen Bonds ◽  
Metal Free ◽  
Potential Applicability ◽  
Selective Substitution ◽  
Snar Reaction

Nucleophilic aromatic substitution (SNAr) reactions can provide metal-free access to synthesize monosubstituted aromatic compounds. We developed efficient SNAr conditions for p-selective substitution of polyfluoroarenes with phenothiazine in the presence of a mild base to afford the corresponding 10-phenylphenothiazine (PTH) derivatives. The resulting polyfluoroarene-bearing PTH derivatives were subjected to a second SNAr reaction to generate highly functionalized PTH derivatives with potential applicability as photocatalysts for the reduction of carbon–halogen bonds.

One-Pot Approach for SNAr Reaction of Fluoroaromatic Compounds with Cyclopropanol

Synlett ◽  
2019 ◽  
Vol 30 (08) ◽  
pp. 982-986
Author(s):  
Hao Jin ◽  
Zhuo Gao ◽  
Shaodong Zhou ◽  
Chao Qian
Keyword(s):  
Aromatic Compounds ◽  
Substitution Reaction ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
One Pot ◽  
Mild Conditions ◽  
Snar Reaction ◽  
Novel Method ◽  
The One ◽  
Application Scope

A novel method for preparing aromatic compounds containing cyclopropoxy via nucleophilic aromatic substitution reaction (SNAr) of fluoroaromatic compounds with cyclopropanol under relatively mild conditions is presented. As compared to the approaches reported previously for preparing 1-(cyclopropyloxy)-2-nitrobenzene, the one proposed in this work is simplified without sacrificing the yields: When the reaction was performed at 75 °C with Cs2CO3 as the base and DMF as solvent, after 6 h the yield was up to 90%. Finally, various fluoroaromatic compounds were employed as substrates for a test that proves a wide application scope of the method.

Studies on the Regioselective Nucleophilic Aromatic Substitution (SNAr) Reaction of 2-Substituted 3,5-Dichloropyrazines

2013 ◽  
Vol 15 (9) ◽  
pp. 2156-2159 ◽  
Author(s):  
Stephanie Scales ◽  
Sarah Johnson ◽  
Qiyue Hu ◽  
Quyen-Quyen Do ◽  
Paul Richardson ◽  
...  
Keyword(s):  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Snar Reaction

Deuterated Aryl Alkyl Ethers Synthesis via Nucleophilic Etherification of Aryl Alkyl Ethers and Thioethers with Deuterated Alcohols

Synlett ◽  
2019 ◽  
Vol 30 (15) ◽  
pp. 1805-1809
Author(s):  
Shuai Li ◽  
Xia Wang ◽  
Xin-Ge Yang ◽  
Gui-Quan Yu ◽  
Xue-Qiang Wang
Keyword(s):  
Transition Metal ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Mechanistic Studies ◽  
Reaction Conditions ◽  
Metal Free ◽  
Wide Range ◽  
Alkyl Ethers

A transition-metal-free etherification protocol that is capable of synthesizing deuterated ethers is described. A wide range of aryl alkyl ethers and thioethers were suitable for this transformation owing to the mild reaction conditions. Besides, a series of sterically bulky deuterated alcohols were successfully incorporated into cyano-substituted arenes. The results of mechanistic studies suggested this reaction might take place via nucleophilic aromatic substitution pathway.

Metal-free Synthesis of Aryl Amines: Beyond Nucleophilic Aromatic Substitution

2016 ◽  
Vol 128 (51) ◽  
pp. 16044-16047 ◽  
Author(s):  
Alexander H. Sandtorv ◽  
David R. Stuart
Keyword(s):  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Metal Free ◽  
Aryl Amines

Transition metal-free construction of trinuclear N-fused hybrid scaffolds by double nucleophilic aromatic substitution under microwave irradiation

2019 ◽  
Vol 21 (24) ◽  
pp. 6590-6593 ◽  
Author(s):  
Pham Duy Quang Dao ◽  
Ho-Jin Lim ◽  
Chan Sik Cho
Keyword(s):  
Transition Metal ◽  
Microwave Irradiation ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Metal Free ◽  
Green Construction ◽  
Free Construction ◽  
Hybrid Scaffolds

A green construction of trinuclear N-fused hybrid scaffolds by transition metal-free double C(sp2)–N coupling of 2-(2-bromoaryl)- and 2-(2-bromovinyl)benzimidazoles with 2-aminoazoles under microwave irradiation has been developed.

scholarly journals N-[4-(1-Methyl-1H-imidazol-2-yl)-2,4′-bipyridin-2′-yl]benzene-1,4-diamine

Molbank ◽  
10.3390/m1030 ◽  
2018 ◽  
Vol 2018 (4) ◽  
pp. M1030 ◽  
Author(s):  
Dhafer Zinad ◽  
Dunya AL-Duhaidahaw ◽  
Ahmed Al-Amiery ◽  
Abdul Kadhum
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
High Performance ◽  
Nucleophilic Aromatic Substitution ◽  
Gas Chromatography Mass Spectrometry ◽  
Aromatic Substitution ◽  
Target Compound ◽  
Chromatography Mass Spectrometry ◽  
Snar Reaction ◽  
Layer Chromatography

N-[4-(1-Methyl-1H-imidazol-2-yl)-2,4′-bipyridin-2′-yl]benzene-1,4-diamine was synthesized with a good yield by the reaction of 2′-chloro-4-(1-methyl-1H-imidazol-2-yl)-2,4′-bipyridine with 4-phenylenediamine. The functionalization of the pyridine was accomplished by a nucleophilic aromatic substitution (SNAr) reaction that afforded the target compound. The synthesized compound was characterized by chemical analysis, which includes nuclear magnetic resonance (NMR) (1H-NMR and 13C-NMR), Thin Layer Chromatography-Mass Spectrometry (TLC-MS), high- performance liquid chromatography (HPLC), Gas Chromatography-Mass Spectrometry (GC-MS), and elemental analysis.

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