Palladium-Catalyzed C–N Cross-Coupling of NH-Heteroarenes and Quaternary Ammonium Salts via C–N Bond Cleavage

2019 ◽  
Vol 23 (8) ◽  
pp. 1679-1685 ◽  
Author(s):  
Hongyi Chen ◽  
Hongqin Yang ◽  
Nutao Li ◽  
Xinghua Xue ◽  
Ze He ◽  
...  
Keyword(s):  
Quaternary Ammonium ◽  
Bond Cleavage ◽  
Cross Coupling ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
Palladium Catalyzed

Palladium-catalyzed carbonylation of benzylic ammonium salts to amides and esters via C–N bond activation

2018 ◽  
Vol 16 (17) ◽  
pp. 3099-3103 ◽  
Author(s):  
Weijie Yu ◽  
Shuwu Yang ◽  
Fei Xiong ◽  
Tianxiang Fan ◽  
Yan Feng ◽  
...  
Keyword(s):  
Quaternary Ammonium ◽  
Bond Activation ◽  
Bond Cleavage ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
Carbonylation Reaction ◽  
Palladium Catalyzed ◽  
First Time ◽  
Acid Esters

An efficient palladium-catalyzed carbonylation reaction of readily available quaternary ammonium salts with CO is reported for the first time to afford arylacetamides and arylacetic acid esters via benzylic C–N bond cleavage.

Palladium-Catalysed Cross-Coupling of Benzylammonium Salts with Boronic Acids under Mild Conditions

Synthesis ◽  
2017 ◽  
Vol 50 (04) ◽  
pp. 793-802 ◽  
Author(s):  
Robert Phipps ◽  
Paul Türtscher ◽  
Holly Davis
Keyword(s):  
Quaternary Ammonium ◽  
Good Yield ◽  
Oxidative Addition ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
Full Account ◽  
Mild Conditions

Herein, we give a full account of the development of the palladium­-catalysed cross-coupling of benzylammonium salts with boronic acids. A range of benzylamine-derived quaternary ammonium salts can be coupled with boronic acids under relatively mild conditions. Our optimization has identified ligands that can be used to chemoselectively cross-couple at the ammonium in the presence of chlorides. We demonstrate that intramolecular palladium-catalysed C–H activation is also a viable pathway for the putative benzyl-Pd(II) intermediate obtained upon oxidative addition and have optimised this to obtain fluorene in good yield.

Chemical transformations of quaternary ammonium salts via C–N bond cleavage

2020 ◽  
Vol 18 (6) ◽  
pp. 1057-1072 ◽  
Author(s):  
Zhong-Xia Wang ◽  
Bo Yang
Keyword(s):  
Quaternary Ammonium ◽  
Bond Cleavage ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
Chemical Transformations

The reaction of quaternary ammonium salts via C–N bond cleavage to construct C–C, C–H and C–heteroatom bonds is summarized.

Synthesis and stability of 1-aminoalkylphosphonic acid quaternary ammonium salts

2021 ◽  
Author(s):  
Tomasz K. Olszewski ◽  
Anna Brol
Keyword(s):  
Phosphonic Acid ◽  
Quaternary Ammonium ◽  
Alkylating Agent ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
Aminoalkylphosphonic Acid

An effective protocol for quaternization of simple 1-aminoalkylphosphonic acids under basic conditions and using Me2SO4 as convenient alkylating agent is reported. In the course of reaction phosphonic acid quaternary ammonium...

scholarly journals Green Accelerated Synthesis, Antimicrobial Activity and Seed Germination Test of Quaternary Ammonium Salts of 1,2-bis(4-pyridyl)ethane

Molecules ◽  
2019 ◽  
Vol 24 (13) ◽  
pp. 2424 ◽  
Author(s):  
Tăbăcaru ◽  
Botezatu ◽  
Horincar ◽  
Furdui ◽  
Dinică
Keyword(s):  
Escherichia Coli ◽  
Triticum Aestivum ◽  
Seed Germination ◽  
Quaternary Ammonium ◽  
Pathogenic Bacteria ◽  
Classical Method ◽  
Triticum Aestivum L ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
Radicle Growth

A family of fifteen quaternary ammonium salts (QAs), bearing the 1,2-bis(4-pyridyl)ethane core, were obtained using for the first time two different green methods, such as microwave (MW) and ultrasounds (US) irradiation, with very good yields and in much shorter times compared to the classical method, and an assay on their antimicrobial action against Escherichia coli (E. coli) was carried out. While 12 to 24 hours were required for complete alkylation of 1,2-bis(4-pyridyl)ethane by reactive halogenated derivatives in anhydrous solvent under reflux conditions, MW and US irradiation reduced the reaction time and the desired products were achieved in a few min. One of the aims of this study was to evaluate the antibacterial potential of the synthesized QAs against pathogenic bacteria, along with their impact on germination activity of wheat seeds (Triticum aestivum L.). The antibacterial activity of the QAs against Escherichia coli was explored by determining the minimum inhibitory concentration (MIC). The MIC values varied from 0.312 to 2.5 mg/mL, highlighting the lowest values attained for the derivatives containing methoxy, chlorine and benzofurane functional groups. The viability of aerobic bacteria was determined with the Tetrazolium/Formazan Test, a method that was found to be the best alternative approach with respect to the difuzimetric method. Seeds of Triticum aestivum L. were used for the evaluation of the germination indicators, such as seed germination (SG), the relative seed germination (RSG), the relative radicle growth (RRG), and the seed germination index (GI). The toxicity studies of QAs 1, 4 and 7, at two different concentrations, showed no inhibitory effect on seed germination.

Interaction of water-insoluble quaternary ammonium salts with the hydrated silica surface

1996 ◽  
Vol 32 (6) ◽  
pp. 331-334
Author(s):  
V. V. Turov ◽  
O. A. Zaporozhets ◽  
O. Yu. Nadzhafova ◽  
V. V. Sukhan
Keyword(s):  
Quaternary Ammonium ◽  
Silica Surface ◽  
Quaternary Ammonium Salts ◽  
Ammonium Salts ◽  
Hydrated Silica
Sign in / Sign up

Export Citation Format

Share Document