Thermally Reversible Dendronized Step-Polymers Based on Sequential Huisgen 1,3-Dipolar Cycloaddition and Diels−Alder “Click” Reactions

2010 ◽  
Vol 43 (3) ◽  
pp. 1270-1276 ◽  
Author(s):  
Nathan W. Polaske ◽  
Dominic V. McGrath ◽  
James R. McElhanon
Keyword(s):  
Diels Alder ◽  
Dipolar Cycloaddition ◽  
Click Reactions

Total Synthesis of (−)- andent-(+)-Vindorosine: Tandem Intramolecular Diels-Alder/1,3-Dipolar Cycloaddition of 1,3,4-Oxadiazoles

2006 ◽  
Vol 118 (4) ◽  
pp. 636-638 ◽  
Author(s):  
Gregory I. Elliott ◽  
Juraj Velcicky ◽  
Hayato Ishikawa ◽  
YongKai Li ◽  
Dale L. Boger
Keyword(s):  
Total Synthesis ◽  
Diels Alder ◽  
Dipolar Cycloaddition

scholarly journals Cycloaddition of Methyl Acrylate with Substituted Pyridinium-3-olates and Pyrazinium-3-olates: 1,3-Dipolar Cycloaddition versus Diels-Alder

2010 ◽  
Author(s):  
Ponnadurai Ramasami ◽  
John Joule ◽  
Luis Domingo ◽  
Sabina Jhaumeer-Laulloo ◽  
Hassan Abdallah ◽  
...  
Keyword(s):  
Methyl Acrylate ◽  
Diels Alder ◽  
Dipolar Cycloaddition

Stoichiometric imbalance-promoted step-growth polymerization based on self-accelerating 1,3-dipolar cycloaddition click reactions

2020 ◽  
Vol 11 (1) ◽  
pp. 125-134 ◽  
Author(s):  
Xianfeng Liu ◽  
Lue Xiang ◽  
Jiayi Li ◽  
Ying Wu ◽  
Ke Zhang
Keyword(s):  
Dipolar Cycloaddition ◽  
Click Reactions ◽  
Step Growth ◽  
Step Growth Polymerization ◽  
Polymerization Method

A stoichiometric imbalance-promoted step growth polymerization method was developed based on self-accelerating 1,3-dipolar cycloaddition click reactions of Sondheimer diyne and varied 1,3-dipoles, such as diazo, sydnone, and nitrone groups.

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.

Improved Protocols for Microwave-Assisted Cu(I)-Catalyzed Huisgen 1,3-Dipolar Cycloadditions

2007 ◽  
Vol 72 (8) ◽  
pp. 1014-1024 ◽  
Author(s):  
Pedro Cintas ◽  
Katia Martina ◽  
Bruna Robaldo ◽  
Davide Garella ◽  
Luisa Boffa ◽  
...  
Keyword(s):  
Heterogeneous Catalysis ◽  
Microwave Irradiation ◽  
Ultrasound Irradiation ◽  
Conventional Heating ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
Click Reactions ◽  
Dipolar Cycloadditions ◽  
Microwave Assisted ◽  
New Applications

The Huisgen 1,3-dipolar cycloaddition of azides and acetylenes catalyzed by Cu(I) salts, leading to 1,2,3-triazoles, is one of the most versatile "click reactions". We have developed a series of optimized protocols and new applications of this reaction starting from several substrates, comparing heterogeneous vs homogeneous catalysis, conventional heating vs microwave irradiation or simultaneous microwave/ultrasound irradiation. Both non-conventional techniques strongly promoted the cycloaddition (bromide → azide → triazole), that could be conveniently performed in a one-pot procedure. This was feasible even with such bulky molecules as functionalized β-cyclodextrins (β-CD), starting from 61-O-tosyl-β-CD or from heptakis[6-O-(tert-butyldimethylsilyl)]-21-O-propargyl-β-CD. "Greener" heterogeneous catalysis with charcoal-supported Cu(II) or Cu(I) (prepared under ultrasound) was advantageously employed.

ChemInform Abstract: An Unexpected Diels-Alder Reaction on the Fullerene Core Rather than an Expected 1,3-Dipolar Cycloaddition.

ChemInform ◽  
2010 ◽  
Vol 33 (31) ◽  
pp. no-no
Author(s):  
Jean-Francois Eckert ◽  
Cyril Bourgogne ◽  
Jean-Francois Nierengarten
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Dipolar Cycloaddition ◽  
Diels Alder Reaction

scholarly journals Platinum(iv) azido complexes undergo copper-free click reactions with alkynes

2018 ◽  
Vol 47 (31) ◽  
pp. 10553-10560 ◽  
Author(s):  
Nicola J. Farrer ◽  
Gitanjali Sharma ◽  
Rachel Sayers ◽  
Evyenia Shaili ◽  
Peter J. Sadler
Keyword(s):  
Dipolar Cycloaddition ◽  
Click Reactions

We report our investigations into the first examples of copper-free 1,3-dipolar cycloaddition (click) reactions of electrophiles with a Pt(iv) azido complex.

scholarly journals Functionalized branched EDOT-terthiophene copolymer films by electropolymerization and post-polymerization “click”-reactions

2015 ◽  
Vol 11 ◽  
pp. 335-347 ◽  
Author(s):  
Miriam Goll ◽  
Adrian Ruff ◽  
Erna Muks ◽  
Felix Goerigk ◽  
Beatrice Omiecienski ◽  
...  
Keyword(s):  
Energy Levels ◽  
Contact Angles ◽  
Redox Properties ◽  
Dipolar Cycloaddition ◽  
Surface Polarity ◽  
Water Contact ◽  
Click Reactions ◽  
Copolymer Films ◽  
Post Functionalization

The electrocopolymerization of 3,4-ethylenedioxythiophene (EDOT) with the branched thiophene building block 2,2′:3′,2″-terthiophene (3T) is presented as a versatile route to functional polymer films. Comparisons to blend systems of the respective homopolymers PEDOT and P3T by in situ spectroelectrochemistry and Raman spectroscopy prove the successful copolymer formation and the access to tailored redox properties and energy levels. The use of EDOT-N3 as co-monomer furthermore allows modifications of the films by polymer analogous reactions. Here, we exemplarily describe the post-functionalization with ionic moieties by 1,3-dipolar cycloaddition (“click”-chemistry) which allows to tune the surface polarity of the copolymer films from water contact angles of 140° down to 40°.

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