Click Assembly of 1,2,3‐Triazole‐Linked Dendrimers, Including Ferrocenyl Dendrimers, Which Sense Both Oxo Anions and Metal Cations

By taking advantage of the orthogonal nature of thiol-ene coupling and anhydride based esterification reactions, a facile and chemoselective strategy to dendritic macromolecules has been developed. The ability to interchange growth steps based on thiol-ene and anhydride chemistry allows the synthesis of fifth-generation dendrimers in only five steps and under benign reaction conditions. In addition, the presented coupling chemistries eliminate the traditional need for protection/deprotection steps and afford dendrimers in high yield and purity. The modularity of this strategy coupled with the latent reactivity of the alkene/hydroxyl chain ends was demonstrated by using different cores (alkene and hydroxyl functional), various AB 2 and CD 2 monomers and a range of chain end groups. As a result, three dendritic libraries were prepared which exhibited tunability of both the chemical functionality and physical properties including the fabrication of PEG hydrogels.

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“…Synthesis of Dendrimer I-[G1]-(OH) 6 . To a vial were added triallyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione 1 (920 mg, 3.69 mmol), 2 (2.…”

Section: Methodsmentioning

confidence: 99%

Accelerated Growth of Dendrimers via Thiol−Ene and Esterification Reactions

et al. 2010

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“…Na química de materiais, a reação "click" vem sendo extensivamente utilizada na obtenção de diversos materiais, tais como dendrí-meros, 37,38,[104][105][106][107] polímeros, [108][109][110][111] fases estacionárias modificadas, [119][120][121][122] organogéis, [123][124][125] macrociclos, [134][135][136] dentre outros. Dendrímeros são moléculas formadas a partir de um núcleo polifuncionalizado através do crescimento radial de camadas, de forma repetitiva.…”

Section: Química De Materiaisunclassified

A reação "click" na síntese de 1,2,3-triazóis: aspectos químicos e aplicações

Freitas¹,

Ruela²,

Pereira³

et al. 2011

Quím. Nova

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“…Since its discovery in 2002, a number of "CuAAC" procedures have been developed for making the synthesis of 1,2,3-triazoles more efficient and environmentally friendly, and mechanisms of 'click' reactions have matured [7]. In most of the "CuAAC" reactions, the Cu (1) species is generated from CuSO 4 and sodium ascorbate; however, the main problem with this method is the requirement of a large quantity of the metal catalyst, which makes its removal difficult at the later stage [8]. Recently, significant attention also has been paid to the use of copper nanoparticles (CuNPs) as catalysts in "CuAAC" reactions in the synthesis of 1,2,3-triazoles; however, most of these reactions require reductants, organic solvents and high loading of CuNPs [911].…”

Section: Introductionmentioning

confidence: 99%

Copper nanoparticle catalyzed regioselective cycloaddition of terminal acetylenes to sodium azide in the presence of O-tosyl fluorocarbohydrate derivatives: assembly of novel enantiopure fluoromonosaccharides with 1,2,3-triazole and 4-phenyl-oxazolidin-2-one subunits

Guesmi

Hamadi

2016

Maced. J. Chem. Chem. Eng.

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A three-component reaction of O-tosyl carbohydrate derivatives with sodium azide and terminal alkynes can be catalyzed by copper nanoparticles under ambient conditions. A series of 1,4-disubstituted-1,2,3-triazoles were obtained regioselectively by this one-pot strategy in good to excellent yields (7090%). The salient features of the present protocol are mild reaction conditions, a shorter reaction time, and its applicability to a wide range of substrates.Keywords: carbohydrates; terminal alkyne; copper nanoparticles; cycloaddition; 1,2,3-triazoles РЕГИОСЕЛЕКТИВНА ЦИКЛОАДИЦИЈА НА ТЕРМИНАЛНИ АЦЕТИЛЕНИ СО НАТРИУМ АЗИД ВО ПРИСУСТВО НА О-ТОЗИЛ-ФЛУОРОКАРБОНАТНИ ДЕРИВАТИ КАТАЛИЗИРАНИ СО БАКАРНИ НАНОЧЕСТИЧКИ: СОСТАВУВАЊЕ НА НОВИ ЕНАНТИОЧИСТИ ФЛУОРОМОНОСАХАРИДИ СО 1,2,3,-ТРИАЗОЛНИ И 4-ФЕНИЛ-ОКСАЗОЛИДИН-2-ОНСКИ ПОДЕДИНИЦИТрокомпонентната реакција на О-тозилокарбонатни деривати со натриум азид и тер-минални алкини може да се катализира со бакарни наночестички во амбиентални услови. Со оваа стратегија е добиена региоселективна серија во еден реакциски сад со добар до одличен принос (70-90%). Главните карактеристики на овој протокол се благите реакциски услови, покусото време на реакција и применливоста на широк опсег на супстрати.

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Click Assembly of 1,2,3‐Triazole‐Linked Dendrimers, Including Ferrocenyl Dendrimers, Which Sense Both Oxo Anions and Metal Cations

Cited by 347 publications

References 31 publications

Accelerated Growth of Dendrimers via Thiol−Ene and Esterification Reactions

Accelerated Growth of Dendrimers via Thiol−Ene and Esterification Reactions

A reação "click" na síntese de 1,2,3-triazóis: aspectos químicos e aplicações

Copper nanoparticle catalyzed regioselective cycloaddition of terminal acetylenes to sodium azide in the presence of O-tosyl fluorocarbohydrate derivatives: assembly of novel enantiopure fluoromonosaccharides with 1,2,3-triazole and 4-phenyl-oxazolidin-2-one subunits

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