Transition-Metal-Free Catalytic Hydrodefluorination of Polyfluoroarenes by Concerted Nucleophilic Aromatic Substitution with a Hydrosilicate

2017 ◽  
Vol 56 (51) ◽  
pp. 16191-16196 ◽  
Author(s):  
Kotaro Kikushima ◽  
Mary Grellier ◽  
Masato Ohashi ◽  
Sensuke Ogoshi
Keyword(s):  
Transition Metal ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Metal Free

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.

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 Transition-metal-free Nucleophilic 211At-astatination of Spirocyclic Aryliodonium Ylides

2021 ◽  
Author(s):  
Keitaro Matsuoka ◽  
Honoka Obata ◽  
Nagatsu Kotaro ◽  
Masahiro Kojima ◽  
Tatsuhiko Yoshino ◽  
...  
Keyword(s):  
Transition Metal ◽  
Substitution Reaction ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Metal Free ◽  
Radiolabeled Compounds

The transition-metal-free 211At-astatination of spirocyclic aryliodonium ylides via a nucleophilic aromatic substitution reaction is described. This method enables the preparation of 211At-radiolabeled compounds derived from multi-functionalized molecules and heteroarenes in...

scholarly journals Base-Promoted SNAr Reactions of Fluoro- and Chloroarenes as a Route to N-Aryl Indoles and Carbazoles

Molecules ◽  
2019 ◽  
Vol 24 (6) ◽  
pp. 1145 ◽  
Author(s):  
Muhammad Iqbal ◽  
Hina Mehmood ◽  
Jiaying Lv ◽  
Ruimao Hua
Keyword(s):  
Transition Metal ◽  
Bond Formation ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Metal Free

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.

scholarly journals Iterative Exponential Growth of Oxygen-Linked Aromatic Polymers Driven by Nucleophilic Aromatic Substitution Reactions

2021 ◽  
Vol 9 ◽  
Author(s):  
Tyler J. Jaynes ◽  
Mona Sharafi ◽  
Joseph P. Campbell ◽  
Jessica Bocanegra ◽  
Kyle T. McKay ◽  
...  
Keyword(s):  
Transition Metal ◽  
Density Functional ◽  
Building Blocks ◽  
Nucleophilic Aromatic Substitution ◽  
Metal Catalyst ◽  
Aromatic Substitution ◽  
Metal Free ◽  
X Ray Crystallography ◽  
Aromatic Polymers ◽  
Leaving Groups

This work presents the first transition metal-free synthesis of oxygen-linked aromatic polymers by integrating iterative exponential polymer growth (IEG) with nucleophilic aromatic substitution (SNAr) reactions. Our approach applies methyl sulfones as the leaving groups, which eliminate the need for a transition metal catalyst, while also providing flexibility in functionality and configuration of the building blocks used. As indicated by 1) 1H-1H NOESY NMR spectroscopy, 2) single-crystal X-ray crystallography, and 3) density functional theory (DFT) calculations, the unimolecular polymers obtained are folded by nonclassical hydrogen bonds formed between the oxygens of the electron-rich aromatic rings and the positively polarized C–H bonds of the electron-poor pyrimidine functions. Our results not only introduce a transition metal-free synthetic methodology to access precision polymers but also demonstrate how interactions between relatively small, neutral aromatic units in the polymers can be utilized as new supramolecular interaction pairs to control the folding of precision macromolecules.

Transition-Metal-Free Homopolymerization of Pyrrolo[2,3-d:5,4-d′]bisthiazoles via Nucleophilic Aromatic Substitution

2021 ◽  
Author(s):  
Somnath Dey ◽  
Salahuddin Attar ◽  
Eric F. Manley ◽  
Salvador Moncho ◽  
Edward N. Brothers ◽  
...  
Keyword(s):  
Transition Metal ◽  
Nucleophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Metal Free

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

Thiolate-Initiated Synthesis of Dibenzothiophenes from 2,2′-Bis(methylthio)-1,1′-Biaryl Derivatives through Cleavage of Two Carbon–Sulfur Bonds

Synlett ◽  
2019 ◽  
Vol 30 (17) ◽  
pp. 1995-1999 ◽  
Author(s):  
Yoshihiro Masuya ◽  
Yuki Kawashima ◽  
Takuya Kodama ◽  
Naoto Chatani ◽  
Mamoru Tobisu
Keyword(s):  
Transition Metal ◽  
Dft Calculations ◽  
Catalytic Reaction ◽  
Nucleophilic Aromatic Substitution ◽  
Metal Catalyst ◽  
Aromatic Substitution ◽  
Transition Metal Catalyst ◽  
Thiolate Anion

A catalytic reaction involving the cleavage of two carbon–sulfur bonds in 2,2′-bis(methylthio)-1,1′-biaryl derivatives is reported. This reaction does not require a transition-metal catalyst and is promoted by a thiolate anion. Notably, based on DFT calculations, the product-forming cyclization step is shown to proceed through a concerted nucleophilic aromatic substitution (CSNAr) mechanism.

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