Aromatic Nitrogen Donors for Efficient Copper(I)–NHC CuAAC under Reductant‐Free Conditions

Teyssot, Marie‐Laure; Nauton, Lionel; Canet, Jean-Louis; Cisnetti, Federico; Chevry, Aurélien; Gautier, Arnaud

doi:10.1002/ejoc.201000046

Cited by 58 publications

(28 citation statements)

References 37 publications

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“…The CuAAC reaction has also been used to 'click' modifications onto the 4-pyridyl position of terdentate ligands, such as dpa derivatives in order to synthesise metal chelators, 76 form Ln(III) luminescent probes, 77 and graft these onto silica nanoparticles. 78 There are many review articles covering this area, such as the use of the CuAAC reaction in construction of dendrimers and polymeric architectures, 79 modification of peptidomimetic oligomers, 80 and construction of higher order interlocked supramolecular structures.…”

Section: Terdentate Ligandsmentioning

confidence: 99%

The btp [2,6-bis(1,2,3-triazol-4-yl)pyridine] binding motif: a new versatile terdentate ligand for supramolecular and coordination chemistry

2014

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Ligands containing the btp [2,6-bis(1,2,3-triazol-4-yl)pyridine] motif have appeared with increasing regularity over the last decade. This class of ligands, formed in a one pot 'click' reaction, has been studied for various purposes, such as for generating d and f metal coordination complexes and supramolecular self-assemblies, and in the formation of dendritic and polymeric networks, etc. This review article introduces btp as a novel and highly versatile terdentate building block with huge potential in inorganic supramolecular chemistry. We will focus on the coordination chemistry of btp ligands with a wide range of metals, and how it compares with other classical pyridyl and polypyridyl based ligands, and then present a selection of applications including use in catalysis, enzyme inhibition, photochemistry, molecular logic and materials, e.g. polymers, dendrimers and gels. The photovoltaic potential of triazolium derivatives of btp and its interactions with anions will also be discussed.

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Section: Terdentate Ligandsmentioning

confidence: 99%

The btp [2,6-bis(1,2,3-triazol-4-yl)pyridine] binding motif: a new versatile terdentate ligand for supramolecular and coordination chemistry

2014

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“…In an extended screening of N-donor additives, the efficiency in the CuAAC test reaction improved in the following order of ligands: neocuproine < 4,7-dimethoxy-1,10-phenanthroline < bathophenanthroline < 1,10-phenanthroline < 4,7-dichloro-1,10-phenanthroline. [71] In 2006, the group of Nolan introduced a new family of monocationic copper(I) NHCcomplexes of general formula [(NHC) 2 Cu]X (X = BF 4 or PF 6 ) as catalysts for hydrosilylation reactions of aldehydes, ketones and esters. [72] These complexes also display very high catalytic activity in CuAAC reactions in water, under neat conditions or as homogeneous catalysts in acetonitrile solution.…”

Section: Catalysts For Cuaac Reactionsmentioning

confidence: 99%

Highly Active Dinuclear Copper Catalysts for Homogeneous Azide–Alkyne Cycloadditions

et al. 2012

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It is better to light a candle than to curse the dark. AbstractThe copper-catalyzed azide-alkyne cycloaddition for the synthesis of 1,4-disubstituted 1,2,3-triazoles (CuAAC) is a variant of Huisgen's 1,3-dipolar cycloaddition which disburdens the thermal reaction from its major drawbacks such as poor regioselectivity, long reaction times and harsh conditions. In contrast to the widely used "black box" reagent mixtures, a molecularly defined, highly active catalyst system for homogeneous CuAAC reactions has been developed in this PhD project. In dependence on the postulated stepwise mechanism, its most important structural feature is the presence of two copper(I) ions irreversibly bound in the same catalyst molecule.A highly modular and profitable synthesis for bistriazolium hexafluorophosphate salts as precursors for the ancillary ligand system was devised. In analogy to the CuAAC catalyst systems of general formula [(NHC) 2 Cu]PF 6 described in literature, novel dinuclear copper(I) complexes with a bistriazolylidene ligand backbone and 1,3-bis(2,6-diisopropylphenyl)-imidazol-2-ylidene (IPr) as sacrificial ligand were prepared.However, these complexes did not show the expected high catalytic activity, most probably due to the strong coordination of the IPr ligands. In consequence, another family of dinuclear copper(I) complexes with m-coordinated acetate as labile ligand was synthesized by reaction of the bistriazolium hexafluorophosphate ligand precursors with copper(I) acetate in the presence of a base.The broad applicability and high catalytic activity of one of these bistriazolylidene dicopper acetate complexes was confirmed by a series of gaschromatographically mo-

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“…The first works that made use of the CuAAC reaction on MSN attempted to make nanocarriers for controlled drug delivery upon specific stimuli. Hence, the pores were capped with supramolecular groups containing cyclodextrin DNA or rotaxanes by anchoring them to the external surface of the nanoparticles using the CuAAC click reaction. Later on, a peroxidase mimic featuring an iron‐based voluminous group was successfully click‐grafted and used for biosensing .…”

Section: Introductionmentioning

confidence: 99%

“…Click reactions,a nd in particular the copper-catalyzeda zide-alkyne cycloaddition (CuAAC) [30,31] which is particularly adapted for solgel materials [32][33][34][35][36][37][38][39][40] due to its wide functional group tolerance [41] and the mild conditions needed, appear to be excellent candidates for the design of such complex systems. The first works that made use of the CuAACr eactiono nM SN attempted to make nanocarriersf or controlled drug delivery upon specific stimuli.H ence,t he pores were capped with supramolecular groups containing cyclodextrin [42,43] DNA [44] or rotaxanes [45] by anchoring them to the external surface of the nanoparticles using the CuAAC click reaction. Later on, ap eroxidase mimic featuring an iron-based voluminous group was successfully click-grafted and used for biosensing.…”

Section: Introductionmentioning

confidence: 99%

Bis‐clickable Mesoporous Silica Nanoparticles: Straightforward Preparation of Light‐Actuated Nanomachines for Controlled Drug Delivery with Active Targeting

Noureddine

Gary‐Bobo

Lichon

et al. 2016

Chemistry A European J

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Bis(clickable) mesoporous silica nanospheres (ca. 100 nm) were obtained by the co-condensation of TEOS with variable amounts (2-5 % each) of two clickable organosilanes in the presence of CTAB. Such nanoparticles could be easily functionalized with two independent functions using the copper-catalyzed alkyne-azide cycloaddition (CuAAC) reaction to transform them into nanomachines bearing cancer cell targeting ligands with the ability to deliver drugs on-demand. The active targeting was made possible after anchoring folic acid by CuAAC click reaction, whereas the controlled delivery was performed by clicked azobenzene fragments. Indeed, the azobenzene groups are able to obstruct the pores of the nanoparticles in the dark whereas upon irradiation in the UV or in the blue range, their trans-to-cis photoisomerization provokes disorder in the pores, enabling the delivery of the cargo molecules. The on-command delivery was proven in solution by dye release experiments, and in vitro by doxorubicin delivery. The added value of the folic acid ligand was clearly evidenced by the difference of cell killing induced by doxorubicin-loaded nanoparticles under blue irradiation, depending on whether the particles featured the clicked folic acid ligand or not.

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Aromatic Nitrogen Donors for Efficient Copper(I)–NHC CuAAC under Reductant‐Free Conditions

Cited by 58 publications

References 37 publications

The btp [2,6-bis(1,2,3-triazol-4-yl)pyridine] binding motif: a new versatile terdentate ligand for supramolecular and coordination chemistry

The btp [2,6-bis(1,2,3-triazol-4-yl)pyridine] binding motif: a new versatile terdentate ligand for supramolecular and coordination chemistry

Highly Active Dinuclear Copper Catalysts for Homogeneous Azide–Alkyne Cycloadditions

Bis‐clickable Mesoporous Silica Nanoparticles: Straightforward Preparation of Light‐Actuated Nanomachines for Controlled Drug Delivery with Active Targeting

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