Competitive formation of homocircuit [3]rotaxanes in synthetically useful yields in the bipyridine-mediated active template CuAAC reaction

scientific article published on 3 February 2015

Competitive formation of homocircuit [3]rotaxanes in synthetically useful yields in the bipyridine-mediated active template CuAAC reaction is …
instance of (P31):
scholarly articleQ13442814

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P356DOI10.1039/C4SC03999H
P8608Fatcat IDrelease_k6baj2wqlzd7dmsv73d5lgxdqi
P932PMC publication ID5645920
P698PubMed publication ID29308153

P50authorStephen M. GoldupQ43266545
Edward A NealQ60015124
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Chemical consequences of mechanical bonding in catenanes and rotaxanes: isomerism, modification, catalysis and molecular machines for synthesisQ29040277
Macrocycle Size Matters: “Small” Functionalized Rotaxanes in Excellent Yield Using the CuAAC Active Template ApproachQ29040928
Copper(I)-catalyzed cycloaddition of organic azides and 1-iodoalkynesQ33762947
Relative contractile motion of the rings in a switchable palindromic [3]rotaxane in aqueous solution driven by radical-pairing interactionsQ33946537
Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azidesQ33958790
Sequence-specific peptide synthesis by an artificial small-molecule machineQ34322067
Direct evidence of a dinuclear copper intermediate in Cu(I)-catalyzed azide-alkyne cycloadditionsQ34337242
Catalytic "active-metal" template synthesis of [2]rotaxanes, [3]rotaxanes, and molecular shuttles, and some observations on the mechanism of the cu(i)-catalyzed azide-alkyne 1,3-cycloaddition.Q34685306
Ligand-accelerated Cu-catalyzed azide-alkyne cycloaddition: a mechanistic reportQ34698368
Active metal template synthesis of rotaxanes, catenanes and molecular shuttlesQ37545389
An efficient approach to mechanically planar chiral rotaxanesQ37688205
Strategies and tactics for the metal-directed synthesis of rotaxanes, knots, catenanes, and higher order linksQ37934797
Progress in the synthesis and exploitation of catenanes since the MillenniumQ38199961
Copper(I)-assembled [3]rotaxane whose two rings act as flapping wingsQ39665502
Diels-Alder active-template synthesis of rotaxanes and metal-ion-switchable molecular shuttlesQ43120017
Active metal template synthesis of [2]catenanesQ43266482
Synthesis of a rotaxane Cu(I) triazolide under aqueous conditionsQ43807665
Passing two strings through the same ring using an octahedral metal center as template: a new synthesis of [3]rotaxanesQ46040927
Adjustable receptor based on a [3]rotaxane whose two threaded rings are rigidly attached to two porphyrinic plates: synthesis and complexation studiesQ46067515
mu-Acetylide and mu-alkenylidene ligands in "click" triazole synthesesQ46791755
Catalytic "click" rotaxanes: a substoichiometric metal-template pathway to mechanically interlocked architecturesQ46944301
Formation of a hetero[3]rotaxane by a dynamic component-swapping strategy.Q51068689
Mechanostereochemistry and the mechanical bond.Q51323444
Efficient assembly of threaded molecular machines for sequence-specific synthesis.Q51745202
Active-Metal Template Synthesis of a Molecular Trefoil KnotQ55883368
Mechanism of the Ligand-Free CuI-Catalyzed Azide-Alkyne Cycloaddition ReactionQ56566538
En Route to a Molecular Sheaf: Active Metal Template Synthesis of a [3]Rotaxane with Two Axles Threaded through One RingQ57384147
An Unusual Nickel−Copper-Mediated Alkyne Homocoupling Reaction for the Active-Template Synthesis of [2]RotaxanesQ57384153
Ligand-assisted nickel-catalysed sp3–sp3 homocoupling of unactivated alkyl bromides and its application to the active template synthesis of rotaxanesQ57384157
Two Axles Threaded Using a Single Template Site: Active Metal Template Macrobicyclic [3]RotaxanesQ57384162
Hybrid organic–inorganic rotaxanes and molecular shuttlesQ57384167
Cadiot–Chodkiewicz Active Template Synthesis of Rotaxanes and Switchable Molecular Shuttles with Weak Intercomponent InteractionsQ57384184
A Catalytic Palladium Active-Metal Template Pathway to [2]RotaxanesQ57384189
[2]Rotaxanes through Palladium Active-Template Oxidative Heck Cross-CouplingsQ57384203
Active-template synthesis of “click” [2]rotaxane ligands: self-assembly of mechanically interlocked metallo-supramolecular dimers, macrocycles and oligomersQ58242800
CuAAC “click” active-template synthesis of functionalised [2]rotaxanes using small exo-substituted macrocycles: how small is too small?Q58242803
The master of chemical topologyQ59405382
Synthesis of Polyyne RotaxanesQ59455437
Homo- and Hetero-[3]Rotaxanes with Two π-Systems Clasped in a Single MacrocycleQ59455499
Synthesis of [2]rotaxanes by the catalytic reactions of a macrocyclic copper complexQ79266787
[3]rotaxane-porphyrin conjugate as a novel supramolecular host for fullerenesQ80165655
Chemical topology: complex molecular knots, links, and entanglementsQ84407436
A new type of insulated molecular wire: a rotaxane derived from a metal-capped conjugated tetrayneQ84447182
A redox-active [3]rotaxane capable of binding and electrochemically sensing chloride and sulfate anionsQ84534513
Synthesis of [3]rotaxanes that utilize the catalytic activity of a macrocyclic phenanthroline-Cu Complex: remarkable effect of the length of the axle precursorQ86177176
Synthesis of rotacatenanes by the combination of Cu-mediated threading reaction and the template method: the dual role of one ligandQ86703916
Synthesis of [2]rotaxanes by the copper-mediated threading reactions of aryl iodides with alkynesQ86774096
P433issue4
P304page(s)2398-2404
P577publication date2015-02-03
P1433published inChemical ScienceQ2962267
P1476titleCompetitive formation of homocircuit [3]rotaxanes in synthetically useful yields in the bipyridine-mediated active template CuAAC reaction
P478volume6

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cites work (P2860)
Q49375307A Fluorescent Ditopic Rotaxane Ion Pair Host
Q42142621A Kinetic Self-Sorting Approach to Heterocircuit [3]Rotaxanes
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Q42542945Active-Metal Template Synthesis of a Halogen-Bonding Rotaxane for Anion Recognition
Q55044495Chelating Rotaxane Ligands as Fluorescent Sensors for Metal Ions.
Q47937652CuAAC in a Distal Pocket: Metal Active-Template Synthesis of Strapped-Porphyrin [2]Rotaxanes.
Q55012058Efficient Multicomponent Active Template Synthesis of Catenanes.
Q55626098High yielding synthesis of 2,2'-bipyridine macrocycles, versatile intermediates in the synthesis of rotaxanes.
Q33588383Macrocyclic shape-persistency of cyclo[6]aramide results in enhanced multipoint recognition for the highly efficient template-directed synthesis of rotaxanes
Q58005002Porphyrinoid rotaxanes: building a mechanical picket fence
Q59133076Stereoselective Synthesis of Mechanically Planar Chiral Rotaxanes
Q48276765Strong and Selective Halide Anion Binding by Neutral Halogen-Bonding [2]Rotaxanes in Wet Organic Solvents
Q60457354The active template approach to interlocked molecules