Copper(i) complexes bearing mesoionic carbene ligands: influencing the activity in catalytic halo-click reactions

2020 ◽  
Vol 49 (43) ◽  
pp. 15504-15510
Author(s):  
Lisa Suntrup ◽  
Julia Beerhues ◽  
Oliver Etzold ◽  
Biprajit Sarkar
Keyword(s):  
Click Reaction ◽  
Carbene Ligands ◽  
Click Reactions ◽  
Dicopper Complexes

A series of mono- and dicopper complexes with mesoionic carbenes are tested as pre-catalysts for the halo-click reaction.

scholarly journals SYNTHESIS OF AN AZIDE–THIOL LINKER FOR HETEROGENEOUS POLYMER FUNCTIONALIZATION VIA THE “CLICK” REACTION

2018 ◽  
Vol 55 (1B) ◽  
pp. 152
Author(s):  
Thuy Thu Truong
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Click Reaction ◽  
Proton Nuclear Magnetic Resonance ◽  
Reaction Yield ◽  
Reaction Conditions ◽  
Click Reactions ◽  
Heterogeneous Polymer ◽  
Ft Ir ◽  
First Time ◽  
Layer Chromatography

In this study, the synthesis of a telechelic linker bearing both azide and thiol functional groups was described. The reaction conditions were investigated to optimize the reaction yield. The product was analyzed using thin layer chromatography (TLC) and proton nuclear magnetic resonance (1H NMR). The employment of the obtained azide–thiol linker in heterogeneous polymer “click” functionalization was demonstrated for the first time, which was monitored by an online FT–IR method. The obtained telechelic azide–thiol linker is envisioned to be useful chemical tools to link macromolecular chains via orthogonal click reactions.

scholarly journals Silver-catalysed azide–alkyne cycloaddition (AgAAC): assessing the mechanism by density functional theory calculations

2016 ◽  
Vol 3 (9) ◽  
pp. 160090 ◽  
Author(s):  
Biswadip Banerji ◽  
K. Chandrasekhar ◽  
Sunil Kumar Killi ◽  
Sumit Kumar Pramanik ◽  
Pal Uttam ◽  
...  
Keyword(s):  
Density Functional ◽  
Click Reaction ◽  
Cycloaddition Reaction ◽  
Triazole Ring ◽  
Density Functional Theory Calculations ◽  
Dipolar Cycloaddition ◽  
Reaction Conditions ◽  
Functional Theory ◽  
Click Reactions ◽  
Counter Ions

‘Click reactions’ are the copper catalysed dipolar cycloaddition reaction of azides and alkynes to incorporate nitrogens into a cyclic hydrocarbon scaffold forming a triazole ring. Owing to its efficiency and versatility, this reaction and the products, triazole-containing heterocycles, have immense importance in medicinal chemistry. Copper is the only known catalyst to carry out this reaction, the mechanism of which remains unclear. We report here that the ‘click reactions’ can also be catalysed by silver halides in non-aqueous medium. It constitutes an alternative to the well-known CuAAC click reaction. The yield of the reaction varies on the type of counter ion present in the silver salt. This reaction exhibits significant features, such as high regioselectivity, mild reaction conditions, easy availability of substrates and reasonably good yields. In this communication, the findings of a new catalyst along with the effect of solvent and counter ions will help to decipher the still obscure mechanism of this important reaction.

Synthesis of allyl cellulose in NaOH/urea aqueous solutions and its thiol–ene click reactions

2015 ◽  
Vol 6 (18) ◽  
pp. 3543-3548 ◽  
Author(s):  
Haoze Hu ◽  
Jun You ◽  
Weiping Gan ◽  
Jinping Zhou ◽  
Lina Zhang
Keyword(s):  
Aqueous Solutions ◽  
Click Reaction ◽  
Allyl Chloride ◽  
Cellulose Derivatives ◽  
Click Reactions

Allyl cellulose can be synthesized from cellulose and allyl chloride in NaOH/urea aqueous solutions and is further used to synthesize a variety of new cellulose derivatives through the thiol–ene click reaction.

scholarly journals Mild Covalent Functionalization of Transition Metal Dichalcogenides with Maleimides: A “Click” Reaction for TMDCs

2018 ◽  
Author(s):  
Mariano Vera-Hidalgo ◽  
Emerson Giovanelli ◽  
Cristina Navío ◽  
Emilio Pérez
Keyword(s):  
Transition Metal ◽  
Chemical Modification ◽  
Biomedical Applications ◽  
Click Reaction ◽  
Transition Metal Dichalcogenides ◽  
Polymer Chemistry ◽  
Covalent Functionalization ◽  
Click Reactions ◽  
Mild Conditions ◽  
Metal Dichalcogenides

The physical properties of ultrathin transition metal dichalcogenides (2D-TMDCs) make them promising candidates as active nanomaterials for catalysis, optoelectronics, and biomedical applications. Chemical modification of TMDCs is expected to be key in modifying/adding new functions that will help make such promise a reality. We present a mild method for the modification of the basal planes of 2H-MoS<sub>2</sub> and WS<sub>2</sub>. We exploit the soft nucleophilicity of sulfur to react it with maleimide derivatives, achieving covalent functionalization of 2H-TMDCs under very mild conditions. Extensive characterization proves that the reaction occurs through Michael addition. Our results adapt one of the most popular “click” reactions in polymer chemistry and biochemistry to obtain a powerful tool for the chemical manipulation of TMDCs.

Polyester nitrile N-oxides for click reactions synthesized with nitroalkane precursors as the initiator

2020 ◽  
Vol 11 (18) ◽  
pp. 3115-3119 ◽  
Author(s):  
Toyokazu Tsutsuba ◽  
Hiromitsu Sogawa ◽  
Toshikazu Takata
Keyword(s):  
Click Reaction ◽  
Polymer Synthesis ◽  
Star Polymer ◽  
Click Reactions ◽  
Catalyst Free

Polyesters that have a nitrile N-oxide function at the initiation end were prepared and applied to a catalyst-free click reaction for star polymer synthesis.

scholarly journals Investigation of the Reactivity of 1-Azido-3-Iodobicyclo[1.1.1]pentane under “Click” Reaction Conditions

2020 ◽  
Author(s):  
Elisabeth Sitte ◽  
Brendan Twamley ◽  
nitika grover ◽  
Mathias Senge
Keyword(s):  
Click Reaction ◽  
Chemical Properties ◽  
Building Blocks ◽  
Dipolar Cycloaddition ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
One Pot ◽  
Click Reactions ◽  
Drug Molecules ◽  
Physical And Chemical

The bicyclo[1.1.1]pentane (BCP) unit exhibits special physical and chemical properties and is under scrutiny as a bioisostere in drug molecules. We employed methodologies for the synthesis of different BCP triazole building blocks from one precursor, 1-azido-3-iodobicyclo[1.1.1]pentane, by Cu(I)-catalyzed 1,3-dipolar cycloaddition (“click”) reactions and integrated cycloaddition-Sonogashira coupling reactions. Thereby, we accessed three classes of substituted BCP derivatives: 1,4-disubstituted triazoles, 5-iodo-1,4,5-trisubstituted triazoles and 5-alkynylated 1,4,5-trisubstituted triazoles. This gives entry to the synthesis of multiply substituted BCP triazoles either on a modular or a one-pot basis. These methodologies were further utilized for appending large chromophoric porphyrin moieties onto the BCP core.

2.1 Introduction to CuAAC

2022 ◽  
Author(s):  
F. F. Ort
Keyword(s):  
Click Reaction ◽  
Cycloaddition Reaction ◽  
Basic Principles ◽  
Click Reactions ◽  
Organic Azides ◽  
General Overview

The basic principles of the copper-catalyzed azide–alkyne cycloaddition reaction (CuAAC), widely considered to be the first click reaction, are described. This involves amongst others the concept of click reactions, the mechanism of CuAAC, the synthesis and reactivity of organic azides and acetylenes, an overview of most commonly used copper(I) catalysts and ligands, the properties of 1,2,3-triazoles and their resemblance to amides, and a general overview of the scope and limitations of this reaction.

scholarly journals Versatile synthesis of end-reactive polyrotaxanes applicable to fabrication of supramolecular biomaterials

2016 ◽  
Vol 12 ◽  
pp. 2883-2892 ◽  
Author(s):  
Atsushi Tamura ◽  
Asato Tonegawa ◽  
Yoshinori Arisaka ◽  
Nobuhiko Yui
Keyword(s):  
Click Reaction ◽  
Benzoic Acids ◽  
Poly Ethylene Glycol ◽  
Azide Group ◽  
Supramolecular Materials ◽  
Click Reactions ◽  
Poly Ethylene ◽  
Substituted Benzoic Acids ◽  
Fluorescent Molecules ◽  
Intracellular Fluorescence

Cyclodextrin (CD)-threaded polyrotaxanes (PRXs) with reactive functional groups at the terminals of the axle polymers are attractive candidates for the design of supramolecular materials. Herein, we describe a novel and simple synthetic method for end-reactive PRXs using bis(2-amino-3-phenylpropyl) poly(ethylene glycol) (PEG-Ph-NH2) as an axle polymer and commercially available 4-substituted benzoic acids as capping reagents. The terminal 2-amino-3-phenylpropyl groups of PEG-Ph-NH2 block the dethreading of the α-CDs after capping with 4-substituted benzoic acids. By this method, two series of azide group-terminated polyrotaxanes (benzylazide: PRX-Bn-N3, phenylazide: PRX-Ph-N3,) were synthesized for functionalization via click reactions. The PRX-Bn-N3 and PRX-Ph-N3 reacted quickly and efficiently with p-(tert-butyl)phenylacetylene via copper-catalyzed click reactions. Additionally, the terminal azide groups of the PRX-Bn-N3 could be modified with dibenzylcyclooctyne (DBCO)-conjugated fluorescent molecules via a copper-free click reaction; this fluorescently labeled PRX was utilized for intracellular fluorescence imaging. The method of synthesizing end-reactive PRXs described herein is simple and versatile for the design of diverse functional PRXs and can be applied to the fabrication of PRX-based supramolecular biomaterials.

Introducing mercaptoacetic acid locking imine reaction into polymer chemistry as a green click reaction

2014 ◽  
Vol 5 (8) ◽  
pp. 2695-2699 ◽  
Author(s):  
Yuan Zhao ◽  
Bin Yang ◽  
Chongyu Zhu ◽  
Yaling Zhang ◽  
Shiqi Wang ◽  
...  
Keyword(s):  
Multicomponent Reactions ◽  
Click Reaction ◽  
High Yield ◽  
Mercaptoacetic Acid ◽  
Polymer Chemistry ◽  
Click Reactions

Some multicomponent reactions (MCRs) are similar to click reactions to give highly selective products with reliable high yield and effective atom utilization, implying that they can also be recognized as click reactions.

scholarly journals Investigation of the Reactivity of 1-Azido-3-Iodobicyclo[1.1.1]pentane under “Click” Reaction Conditions

2020 ◽  
Author(s):  
Elisabeth Sitte ◽  
Brendan Twamley ◽  
nitika grover ◽  
Mathias Senge
Keyword(s):  
Click Reaction ◽  
Chemical Properties ◽  
Building Blocks ◽  
Dipolar Cycloaddition ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
One Pot ◽  
Click Reactions ◽  
Drug Molecules ◽  
Physical And Chemical

The bicyclo[1.1.1]pentane (BCP) unit exhibits special physical and chemical properties and is under scrutiny as a bioisostere in drug molecules. We employed methodologies for the synthesis of different BCP triazole building blocks from one precursor, 1-azido-3-iodobicyclo[1.1.1]pentane, by Cu(I)-catalyzed 1,3-dipolar cycloaddition (“click”) reactions and integrated cycloaddition-Sonogashira coupling reactions. Thereby, we accessed three classes of substituted BCP derivatives: 1,4-disubstituted triazoles, 5-iodo-1,4,5-trisubstituted triazoles and 5-alkynylated 1,4,5-trisubstituted triazoles. This gives entry to the synthesis of multiply substituted BCP triazoles either on a modular or a one-pot basis. These methodologies were further utilized for appending large chromophoric porphyrin moieties onto the BCP core.

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