Efficient Metal-Free Norbornadiene–Maleimide Click Reaction for the Formation of Molecular Bottlebrushes

2021 ◽  
Author(s):  
Zheqi Li ◽  
Wangmeng Hou ◽  
Yuanchao Li ◽  
Jianxiong Xu ◽  
Yi Shi ◽  
...  
Keyword(s):  
Click Reaction ◽  
Metal Free

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.

Synthesis and Characterization of a Novel Linear Benzoxazine-Containing Polytriazole via Metal-Free Click Reaction and its Self-Crosslinking Behavior

2012 ◽  
Vol 557-559 ◽  
pp. 973-978
Author(s):  
Zhong Yi Xu ◽  
Lei Du ◽  
Li Qiang Wan ◽  
Fa Rong Huang
Keyword(s):  
Click Reaction ◽  
Decomposition Temperature ◽  
Linear Polymer ◽  
The Novel ◽  
Metal Free ◽  
Crosslinked Polymer ◽  
Degradation Behaviors ◽  
Ft Ir ◽  
Increasing Temperature

A novel linear benzoxazine-containing polytriazole was successfully synthesized via metal-free click reaction. Benefited from the advantages of click reaction, the synthesis procedure was easily and efficiently. The linear polymer could be transformed into crosslinked structure after ring-opening polymerization of oxazine induced by the increasing temperature. The FT-IR characterization verified the structure transformation between linear and crosslinked polymer. Moreover, the thermal properties and thermal degradation behaviors of linear polymer and the corresponding crosslinked polymer were studied by DSC and TGA. The novel polytriazole was proved to be a kind of thermal stable polymers with high thermal decomposition temperature (Td5over 300°C).

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 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.

Post-Functionalization of an Anderson-Type Polyoxomolybdate Using a Metal-Free Diels-Alder Click Reaction

2013 ◽  
Vol 2013 (8) ◽  
pp. 1381-1389 ◽  
Author(s):  
Hai-Kuan Yang ◽  
Ming-Ming Su ◽  
Li-Jun Ren ◽  
Jing Tang ◽  
Yu-Kun Yan ◽  
...  
Keyword(s):  
Click Reaction ◽  
Diels Alder ◽  
Metal Free ◽  
Post Functionalization

Facile Solvent- and Metal-Free Synthesis of Polymers Including Triazole by Click Reaction

2018 ◽  
Vol 3 (15) ◽  
pp. 4124-4128
Author(s):  
Reza Ranjbar-Karimi ◽  
Ali Mehrafarin ◽  
Amir Mahyari ◽  
Hossein Mehrabi
Keyword(s):  
Click Reaction ◽  
Metal Free

Metal free thiol–maleimide ‘Click’ reaction as a mild functionalisation strategy for degradable polymers

2008 ◽  
pp. 5158 ◽  
Author(s):  
Ryan J. Pounder ◽  
Matthew J. Stanford ◽  
Paul Brooks ◽  
Stephen P. Richards ◽  
Andrew P. Dove
Keyword(s):  
Click Reaction ◽  
Degradable Polymers ◽  
Metal Free ◽  
Free Thiol

scholarly journals Selective removal of toxic organic dyes using Trӧger base-containing sulfone copolymers made from a metal-free thiol-yne click reaction followed by oxidation

RSC Advances ◽  
2021 ◽  
Vol 11 (34) ◽  
pp. 21170-21178
Author(s):  
Noorullah Baig ◽  
Suchetha Shetty ◽  
Moustafa Sherief Moustafa ◽  
Saleh Al-Mousawi ◽  
Bassam Alameddine
Keyword(s):  
Methylene Blue ◽  
Selective Oxidation ◽  
Removal Efficiency ◽  
Organic Dyes ◽  
Click Reaction ◽  
Selective Removal ◽  
Metal Free ◽  
Free Thiol ◽  
Base Units

Copolymers TCP1–3 with Trӧger's base units and aryl thioether groups were made via a click reaction. Selective oxidation of the thioethers into sulfone groups afforded TCP4–6 which display up to 100% removal efficiency of methylene blue from water.

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