The Rise of Azide–Alkyne 1,3-Dipolar 'Click' Cycloaddition and its Application to Polymer Science and Surface Modification

2007 ◽  
Vol 60 (6) ◽  
pp. 384 ◽  
Author(s):  
Richard A. Evans
Keyword(s):  
Surface Modification ◽  
Atom Transfer Radical Polymerization ◽  
Historical Context ◽  
Dipolar Cycloaddition ◽  
Polymer Science ◽  
Surface Immobilization ◽  
Terminal Alkyne ◽  
New Methods ◽  
High Yields ◽  
Constant Interest

New methods to synthesize and functionalize polymers are of constant interest to the polymer scientist. The 1,3-dipolar cycloaddition between an azide and terminal alkyne has received much attention since the reports that copper(i) provides high yields and regioselective synthesis of 1,4-substituted 1,2,3-triazoles. This coupling chemistry has been rapidly adopted by polymer scientists in the synthesis and post-polymerization modification of polymers. This Review will provide the historical context of the recent development of the copper-mediated azide–alkyne cycloaddition and its use in polymer science, particularly in dendrimer synthesis/functionalization, surface immobilization/modification, orthogonally functionalizing polymers, and its integration with ATRP (atom transfer radical polymerization).

scholarly journals A Review on Development of Ceramic-Graphene Based Nanohybrid Composite Systems in Biological Applications

2021 ◽  
Vol 9 ◽  
Author(s):  
Michał Jakubczak ◽  
Agnieszka M. Jastrzębska
Keyword(s):  
Drinking Water ◽  
Surface Modification ◽  
Biological Applications ◽  
Water Decontamination ◽  
Industrial Practice ◽  
Composite Systems ◽  
New Methods ◽  
Rational Development ◽  
Nanohybrid Composite ◽  
Materials Used

Graphene-based nanocomposites constitute an interesting and promising material for various applications. Intensive progress in the development of this group of materials offers an opportunity to create new systems useful for drinking water decontamination or other biotechnological applications. Nanohybrid structures of graphene-ceramic systems can be obtained using covalent graphene surface modification with nanoparticles (NPs) of ceramic and/or co-deposition of metals with selected morphology and chemistry. The present paper systematizes the associated bio-related knowledge and inspires future development of graphene/NPs systems. Emerging knowledge and unique research techniques are reviewed within designing the required nanocomposite structure and chemical composition, development and optimization of new methods of covalent surface modification of graphene with NPs as well as analysis of mechanisms governing the formation of covalent bonding. Further, innovative research tools and methodologies are presented regarding the adjustment of functionalities of materials used for the application in drinking water decontamination or biocidal composites. This study provides a comprehensive base for rational development of more complex, hybrid graphene-based nanomaterials with various bio-functionalities that can be further applied in industrial practice.

scholarly journals Cu(ii)/DM-Segphos catalyzed asymmetric 1,3-dipolar cycloaddition of benzoisothiazole-2,2-dioxide-3-ylidenes and azomethine ylides

RSC Advances ◽  
2017 ◽  
Vol 7 (18) ◽  
pp. 10816-10820 ◽  
Author(s):  
Feifei Li ◽  
Guorui Cao ◽  
Yanfeng Gao ◽  
Dawei Teng
Keyword(s):  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
High Yields

Cu(OTf)2/DM-Segphos catalyzed asymmetric 1,3-dipolar cycloaddition of benzoisothiazole-2,2-dioxide-3-ylidenes and azomethine ylides was studied. The spiropyrrolidinyl-benzoisothiazolines were obtained in high yields with up to >99 : 1 dr and 99% ee.

Regiospecific Palladium-Catalyzed Cross-Coupling Reactions Using the Operational Equivalent of 1,3-Dilithiopropyne

Synthesis ◽  
2020 ◽  
Vol 52 (16) ◽  
pp. 2387-2394 ◽  
Author(s):  
Jorge A. Cabezas ◽  
Natasha Ferllini
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Terminal Alkyne ◽  
Copper Iodide ◽  
Reaction Conditions ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
High Yields

A regiospecific palladium-catalyzed cross-coupling reaction using the operational equivalent of the dianion 1,3-dilithiopropyne, with aromatic iodides is reported. This reaction gives high yields of 1-propyn-1-yl-benzenes and 2-(propyn-1-yl)thiophenes in the presence of catalytic amounts of palladium(0) or (II) and stoichiometric amounts of copper iodide. No terminal alkyne or allene isomers were detected. Reaction conditions were very mild and several functional groups were tolerated.

Neue effektive Synthesemethoden für UCl5 und UCl6 / New Effective Methods for the Synthesis of UCl5 and UCl6

1982 ◽  
Vol 37 (4) ◽  
pp. 524-526 ◽  
Author(s):  
Klaus Redieß ◽  
Wolfgang Sawodny
Keyword(s):  
Low Temperatures ◽  
New Methods ◽  
High Yields

New methods are reported which allow the synthesis of pure UCl5 and UCl6 in high yields. UCl5 is obtained by chlorination of UF5 · 2 SbF5 with BCl3 at low temperatures, UCl6 by direct chlorination of UCl4 in SbCl5.

Decarboxylative-Mediated Regioselective 1,3-Dipolar Cycloaddition for Diversity-Oriented Synthesis of Structurally exo′-Selective Spiro[oxindole-pyrrolidine-dihydrocoumarin] Hybrids

Synthesis ◽  
2020 ◽  
Author(s):  
Ying Zhou ◽  
Xiong-Wei Liu ◽  
Shun-Qin Chang ◽  
Qi-Lin Wang ◽  
Shuang Chen ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Transition State ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Diversity Oriented Synthesis ◽  
Biologically Relevant ◽  
Good Substrate ◽  
Quaternary Center ◽  
Substrate Tolerance ◽  
High Yields

A general and practical three-component regioselective 1,3-dipolar cycloaddition of 3-amino-oxindole-based azomethine ylides and coumarins has been developed. This reaction displayed good substrate tolerance and gave a diverse array of biologically relevant spiro[ox-­i­ndole-pyrrolidine-dihydrocoumarin] derivatives bearing four contiguous stereocenters including one spiro quaternary center in moderate to high yields (up to 90%) with high diastereoselectivities (up to 15:1 dr). It is based on the application of carboxylic acid activated coumarins as dienophiles followed by a decarboxylation process. The possible mechanism of the 1,3-dipolar cycloaddition is proposed via an exo′-transition state. Furthermore, this is the first example of decarboxylative-mediated regioselective 1,3-dipolar cycloaddition of 3-amino-oxindole-based azomethine ylides and coumarins.

Concise Synthesis of Tryptanthrin Spiro Analogues with In Vitro Antitumor Activity Based on One-Pot, Three-Component 1,3-Dipolar Cycloaddition of Azomethine Ylides to Сyclopropenes

Synthesis ◽  
2018 ◽  
Vol 51 (03) ◽  
pp. 713-729 ◽  
Author(s):  
Vitali Boitsov ◽  
Alexander Stepakov ◽  
Alexander Filatov ◽  
Nickolay Knyazev ◽  
Stanislav Shmakov ◽  
...  
Keyword(s):  
Antitumor Activity ◽  
Azomethine Ylides ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
Economic Method ◽  
Reaction Proceeds ◽  
High Yields

A simple, efficient and atom-economic method has been developed for the synthesis of complex alkaloid-like compounds with spiro-fused indolo[2,1-b]quinazoline and cyclopropa[a]pyrrolizine or 3-azabicyclo[3.1.0]hexane moieties. We have found that one-pot, three-component 1,3-dipolar cycloaddition reactions allow the desired products to be obtained from various cyclopropene derivatives with tryptanthrin-derived azomethine ylides generated in situ, in good to high yields and excellent diastereoselectivity. The possibility of ylide generation was exemplified by using α-amino acids (l-proline, l-4-thiazolidincarboxylic acid) and simplest peptides (dipeptide Gly-Gly, tripeptide Gly-Gly-Gly). Quantum chemical investigations indicate that the reaction proceeds through the S-shaped azomethine ylide, the interaction of which with cyclopropenes proceeds via a less sterically hindered endo-transition state. The antitumor activity of some of spiro-tryptanthrin derivatives against erythroleukemia (K562), cervical carcinoma (HeLa) and colon carcinoma (CT26) cell lines was evaluated in vitro by MTS-assay.

Enzymatic synthesis of ionic responsive lignin nanofibres through surface poly(N-isopropylacrylamide) immobilization

2014 ◽  
Vol 16 (8) ◽  
pp. 3890-3898 ◽  
Author(s):  
Guangzheng Gao ◽  
Muzaffer A. Karaaslan ◽  
John F. Kadla ◽  
Frank Ko
Keyword(s):  
Surface Modification ◽  
Atom Transfer Radical Polymerization ◽  
Radical Polymerization ◽  
Enzymatic Synthesis ◽  
Atom Transfer ◽  
Aqueous Conditions

Surface modification of electrospun lignin nanofibres with poly(N-isopropylacrylamide) (PNIPAM) was conducted through surface-initiated atom transfer radical polymerization (ATRPase) using various biocatalysts under aqueous conditions.

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