1,3-Dipolar cycloaddition between a metal–azide (Ph3PAuN3) and a metal–acetylide (Ph3PAuCCPh): an inorganic version of a click reaction

2011 ◽  
Vol 40 (32) ◽  
pp. 8140 ◽  
Author(s):  
Trevor J. Del Castillo ◽  
Soumya Sarkar ◽  
Khalil A. Abboud ◽  
Adam S. Veige
Keyword(s):  
Click Reaction ◽  
Dipolar Cycloaddition ◽  
Metal Azide

1,3-dipolar cycloaddition in the synthesis of glycoconjugates of natural chlorins and bacteriochlorins

2009 ◽  
Vol 13 (03) ◽  
pp. 336-345 ◽  
Author(s):  
Mikhail A. Grin ◽  
Ivan S. Lonin ◽  
Anna A. Lakhina ◽  
Elena S. Ol'shanskaya ◽  
Alexey I. Makarov ◽  
...  
Keyword(s):  
Triple Bond ◽  
Tautomeric Form ◽  
Click Reaction ◽  
Copper Cation ◽  
Water Soluble ◽  
Dipolar Cycloaddition ◽  
Nmr Studies ◽  
Metal Free ◽  
Cu Complex ◽  
Derivatives Of

Glucose-, galactose- and lactose-containing photosensitizers based on derivatives of chlorophyll a and bacteriochlorophyll a were synthesized with the use of [3+2] cycloaddition between sugar azides and triple bond derivatives of chlorins and bacteriochlorins. Unlike bacteriochlorin cycloimide, chlorin was detected to form a Cu -complex during the click reaction. An approach to the synthesis of metal-free glycosylated chlorins was developed with the use of "protection" by Zn 2+ cation and subsequent demetalation. It is based on the action of alkynyl chlorin e6 derivative Zn -complex, which is resistant to the substitution by copper cation. Bacteriochlorin p cycloimide conjugate with per-acetylated β-D-lactose was obtained and shown to become water-soluble after unblocking of the lactose hydroxy functions. NMR studies allowed for the elucidation of structure, tautomeric form and conformation of the obtained compounds.

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.

scholarly journals Cupric oxide nanowires on three-dimensional copper foam for application in click reaction

RSC Advances ◽  
2017 ◽  
Vol 7 (16) ◽  
pp. 9567-9572 ◽  
Author(s):  
Chunxia Wang ◽  
Fan Yang ◽  
Yan Cao ◽  
Xing He ◽  
Yushu Tang ◽  
...  
Keyword(s):  
Thermal Oxidation ◽  
Heterogeneous Catalysts ◽  
Click Reaction ◽  
Cupric Oxide ◽  
Three Dimensional ◽  
Dipolar Cycloaddition ◽  
Oxide Nanowires ◽  
Copper Foam ◽  
Additional Support ◽  
Cu Foam

CuO nanowires can be synthesized by facile thermal oxidation of 3D Cu foam in air, which were found to be effective heterogeneous catalysts for the 1,3-dipolar cycloaddition reactions without using any additional support and bases.

A Potential New RAFT - Click Reaction or a Cautionary Note on the Use of Diazomethane to Methylate RAFT-synthesized Polymers

2011 ◽  
Vol 64 (4) ◽  
pp. 433 ◽  
Author(s):  
Ming Chen ◽  
Graeme Moad ◽  
Ezio Rizzardo
Keyword(s):  
Molecular Weight ◽  
Methyl Methacrylate ◽  
Room Temperature ◽  
Click Reaction ◽  
Raft Polymerization ◽  
Dipolar Cycloaddition ◽  
Low Molecular Weight ◽  
Similar Reaction ◽  
Poly Methyl Methacrylate ◽  
End Groups

It has been found that diazomethane undergoes a facile 1,3‐dipolar cycloaddition with both dithiobenzoate RAFT agents and the dithiobenzoate end‐groups of polymers formed by RAFT polymerization. Thus, 2‐cyanoprop‐2‐yl dithiobenzoate on treatment with diazomethane at room temperature provided a mixture of stereoisomeric 1,3‐dithiolanes in near quantitative (>95%) yield. A low‐molecular‐weight RAFT‐synthesized poly(methyl methacrylate) with dithiobenzoate end‐groups underwent similar reaction as indicated by immediate decolourization and a quantitative doubling of molecular weight. Higher‐molecular‐weight poly(methyl methacrylate)s were also rapidly decolourized by diazomethane and provided a product with a bimodal molecular weight distribution. Under similar conditions, the trithiocarbonate group does not react with diazomethane.

scholarly journals Metal-Free Click Synthesis of Functional 1-Substituted-1,2,3-Triazoles

2019 ◽  
Author(s):  
Marie-Claire Giel ◽  
Christopher J. Smedley ◽  
Emily R. R. Mackie ◽  
Taijie Guo ◽  
Jiajia Dong ◽  
...  
Keyword(s):  
Click Reaction ◽  
Dipolar Cycloaddition ◽  
Chromatographic Purification ◽  
Metal Free ◽  
Organic Azides ◽  
Novel Method ◽  
Fluoride Salts ◽  
Sulfonyl Fluoride ◽  
Click Synthesis ◽  
Selection Of

The 1,2,3-triazole group is one of the most important connective linkers and functional aromatic heterocycles in modern chemistry. The boom in growth of, in particular, 1,4-disubstituted triazole products since the early 2000’s, can be largely attributed to the birth of click chemistry and the discovery of the Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC). Yet the synthesis of relatively simple, albeit important, 1-substituted-1,2,3-triazoles, has been surprisingly more challenging. We report a straightforward and scalable click-protocol for the synthesis of 1-substituted-1,2,3-triazoles from organic azides and the bench stable acetylene-surrogate, ethenesulfonyl fluoride (ESF). The transformation proceeds through a thermal 1,3-dipolar cycloaddition of the azide and ESF to give a sulfonyl fluoride substituted triazoline, that itself spontaneously aromatizes through formal loss of HF/SO<sub>2 </sub>to give the stable triazole products with excellent fidelity. The new click reaction tolerates a wide selection of substrates and proceeds smoothly under metal-free conditions to give the products in excellent yield, and without need for additives or chromatographic purification. Further, under controlled conditions, the 1-substituted-1,2,3-triazole products undergo Michael reaction with a second equivalent of ESF to give the unprecedented 1-substituted triazolium sulfonyl fluoride salts, demonstrating the versatility and orthogonal reactivity of ESF. The importance of this novel method is evidenced through the late-stage modification of several drugs and drug fragments, including the synthesis of a new improved derivative of the famous antibiotic, chloramphenicol.

scholarly journals "Click" chemistry as a tool to create novel biomaterials: a short review

2017 ◽  
Vol 1 (1) ◽  
pp. 22-34
Author(s):  
Mariana Barbosa ◽  
Cristina Martins ◽  
Paula Gomes
Keyword(s):  
Click Chemistry ◽  
Biomedical Applications ◽  
Recent Literature ◽  
Click Reaction ◽  
Cycloaddition Reaction ◽  
Polymeric Materials ◽  
Short Review ◽  
Dipolar Cycloaddition ◽  
Functionalization Of Polymers ◽  
Grafting Modification

In recent years, there has been a growing demand for novel strategies for biomedical applications. Chitosan is a typical cationic amino-containing polysaccharide that has been widely used due to its unique properties. The grafting modification of chitosan has been explored as an interesting method to develop multifunctional novel chitosan hybrid materials for drug delivery, tissue engineering, and other biomedical applications. Recently, “click” chemistry has been introduced into the synthesis of polymeric materials with well-defined and complex chain architectures. The Huisgen’s 1,3-dipolar cycloaddition reaction between alkynes and azides yielding triazoles is the principal example of a “click” reaction. Bioconjugation, surface modification, and orthogonal functionalization of polymers were successfully performed through this chemoselective reaction. In recent literature interest has been shown in this cycloaddition for the modification of polysaccharides, however, only a few chitosan graft copolymers have been synthesized by this technique.

Simple, stepwise and alternative syntheses of indolyl triazoles via Huisgen,s 1, 3-dipolar cycloaddition reaction

2020 ◽  
Vol 17 ◽  
Author(s):  
Ch. Venkata Ramana Reddy ◽  
G. Ganga Reddy
Keyword(s):  
Reaction Time ◽  
Addition Reaction ◽  
Click Reaction ◽  
Cycloaddition Reaction ◽  
Sodium Ascorbate ◽  
Dipolar Cycloaddition ◽  
Spectroscopic Methods ◽  
Aryl Azides ◽  
Simple Processing ◽  
High Yields

: A series of new 2-((1-((1-(4-methoxy-3-nitrophenyl)-1H-1,2,3-triazol-4-yl)methyl)1H-indol-3-yl)me thylene)malononitrile derivatives were synthesized by the 1,3 dipolar cyclo addition reaction (click reaction) of 2-((1-(prop-2-yn-1-yl)-1H-indol-3-yl)methylene)malononitrile with different aryl azides in the presence of sodium ascorbate and copper sulphate in good yields. The advantages of this method are efficient, clean, high yields, easy workup procedures and shorter reaction time. These reactions are very facile giving products by simple processing that does not require purification by column chromatography. All the newly synthesized compounds were confirmed by spectroscopic methods.

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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